Organometallic chemistry is an interdisciplinary science which continues to grow at a rapid pace. Although there is continued interest in synthetic and structural studies the last decade has seen a growing interest in the potential of organometallic chemistry to provide answers to problems in catalysis synthetic organic chemistry and also in the development of new materials. This Specialist Periodical Report aims to reflect these current interests reviewing progress in theoretical organometallic chemistry, main group chemistry, the lanthanides and all aspects of transition metal chemistry. Specialist Periodical Reports provide systematic and detailed review coverage of progress in the major areas of chemical research. Written by experts in their specialist fields the series creates a unique service for the active research chemist, supplying regular critical in-depth accounts of progress in particular areas of chemistry. For over 80 years the Royal Society of Chemistry and its predecessor, the Chemical Society, have been publishing reports charting developments in chemistry, which originally took the form of Annual Reports. However, by 1967 the whole spectrum of chemistry could no longer be contained within one volume and the series Specialist Periodical Reports was born. The Annual Reports themselves still existed but were divided into two, and subsequently three, volumes covering Inorganic, Organic and Physical Chemistry. For more general coverage of the highlights in chemistry they remain a 'must'. Since that time the SPR series has altered according to the fluctuating degree of activity in various fields of chemistry. Some titles have remained unchanged, while others have altered their emphasis along with their titles; some have been combined under a new name whereas others have had to be discontinued. The current list of Specialist Periodical Reports can be seen on the inside flap of this volume.

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Organometallic Chemistry Volume 1

A Review of the Literature Published during 1971

By E. W. Abel, F. G. A. Stone

The Royal Society of Chemistry

Chapter 1 Group I. The Alkali and Coinage Metals By B. C. Crosse, 
Chapter 2 Group II. The Alkaline Earths and Zinc and its Congeners By B. C. Crosse, 
Chapter 3 Group III. Boron, Aluminium, Gallium, Indium, and Thallium By J. P. Maher, 
Chapter 4 Group III. The Carboranes By T. Onak, 104, 
Chapter 5 Group IV. The Silicon Group By D. A. Armitage, 
Chapter 6 Metal Carbonyls By E. W. Abel and F. G. A. Stone, 
Chapter 7 Organometallic Compounds containing Metal-Metal Bonds By J. D. Cotton, 
Chapter 8 Substitution Reactions of Metal and Organometal Carbonyls with Group V and VI Donor Ligands By R. J. Mawby, 
Chapter 9 Carbene, Nitrene, and Related Complexes By J. A. Connor, 
Chapter 10 Complexes containing Metal–Carbon σ-Bonds By M. I. Bruce, 
Chapter 11 Hydrocarbon–Metal π-Complexes By M. A. Bennett, 
Chapter 12 π-Allylic Complexes By M. Green, 
Chapter 13 π-Cyclopentadlenyl, Arene, and Related Compounds By R. J. Mawby, 
Chapter 14 Substitution Reactions of Hydrocarbon–Metal π-Complexes By M. I. Bruce, 
Chapter 15 Oxidative-addition and Related Reactions By M. Green, 
Chapter 16 Homogeneous Catalysis By F. J. McQuillin, 
Chapter 17 X-Ray and Electron Diffraction Studies of Organometallic Compounds By R. F. Bryan, 
Author Index, 501,

CHAPTER 1

Group I. The Alkali and Coinage Metals

BY B. C. CROSSE

1 Lithium

Structural and Bonding Studies. — Whereas lithium alkyls are highly associated in hydrocarbon solvents, the addition of tetrahydrofuran leads to a large conductivity increase, indicating ionization. The nature of the ions formed has been established by electrodialysis of labelled n-butyl-lithium solutions in tetrahydrofuran. An equilibrium is established between the solvated dimer, monomer, and free ions:

Bu- + Li+, THF [??] BuLi,THF [??] (BuLi)2, THF [??] Bu- + Li2Bu+, THF

The addition of lithium 2-methoxyethoxide or 2-dimethylaminoethoxide greatly enhances the ionic nature of lithium alkyls. The resulting electronic spectra are those expected for solvent-separated ion pairs. The presence of species of the type RLi,2MeOC2H4OLi is indicated, and the term 'co-ordination-agent-separated' ion pair is suggested, to distinguish them from solvent-separated species.

The structures of some aromatic ion pairs, including cyclopentadienyl-lithium and 1-phenylallyl-lithium, have been studied by n.m.r. spectroscopy. The 7Li chemical shift is related to the distance between the plane of the aromatic anion and the lithium cation located above its π-electron cloud. N.m.r. has also been used to study the nature of the bonding in benzyllithium and its derivative n-C5H11CPh2Li. The variation of the n.m.r. data with solvent points to an appreciable sp3 character for the α-carbons, but the variation is less marked in the diphenylhexyl compound, due to the larger π-system, which favours sp2 character. A similar study of n-C5H11CPh2Li and n-C3H7CPh2Li was interpreted in terms of a dimeric structure in benzene solution and solvent-separated ion pairs in tetrahydrofuran.

The sole X-ray structural determination was of the polynuclear compound LiBMe4. In this, each lithium and each boron atom is four-co-ordinate and linked to a terminal methyl group, two bridging methyls, and an almost linear bridging methyl group in which the lithium-carbon bond length is the shortest known. Measurements of 7Li spin–lattice relaxation times suggested that (Me3SiCH2Li)4 is distorted from tetrahedral symmetry, and so even is the methyl-lithium tetramer above 0 °C. A Raman study of the t-butyl-lithium tetramer indicated that the extent of metal–metal bonding in this compound is insignificant.

n-Pentyl- and n-octyl-lithium appear to exist in solution as hexamers; this is deduced from the extent of their lowering of the vapour pressure of benzene. In contrast, phenyl- and p-tolyl-lithium in ether solution appear not to be associated. A variable-temperature 7Li n.m.r. study of the exchange reaction between them showed that only two species exist, and these are in rapid equilibrium. If there were any association, one would expect also mixed species such as p-MexC6H4Li2Ph.

The exchange reaction between phenyl-lithium and bromobenzene has also been studied. The addition of lithium bromide had an inhibiting effect on the exchange of phenyl groups, and this was explained by the formation of a phenyl-lithium–lithium bromide complex, for which a 1:1 stoicheiometry was established. The previous irreproducibility of results from phenyl-lithium exchange reactions was therefore attributed to different methods of preparation, and the resulting presence or otherwise of this complex. In the halogen–metal exchange reaction of 1- and 2-fluoronaphthalenes with lithium, the presence of the fluoronaphthalene radical anions has been detected below -30 °C by e.s.r. spectroscopy.

Polylithio-compounds. — Some polynuclear arenes undergo facile polylithiation by n-butyl-lithium and NNN'N'-tetramethylethylenediamine (TMED). Deuteriation experiments and mass spectral analysis show that biphenyl and indene will substitute up to six hydrogen atoms by lithium, while anthracene and fluorene form traces of the perlithio-derivatives as well as less highly metallated species. In each case the predominant species contained about three lithium atoms per molecule.

A perlithio-compound C5Li4 was obtained from the butyl-lithium–TMED treatment of penta-l,3-diyne. Hydrolysis led to a mixture of penta-1,4-diyne, penta-1,2-dien-4-yne, and some of the initial diacetylene. Traces of the perlithio-compound C9Li8 may have been formed when 1-phenylpropyne was heated with a fifty-fold excess of butyl-lithium, but the main products were C9H2Li6 and C9H3Li5. Several other polylithio-species were also detected. The presence of TMED reduced the degree of lithiation. Butyllithium in ether at 0 °C gave only the monolithio-compound. Derivatization by quenching with water, deuterium oxide, formaldehyde, acetone, or trimethylchlorosilane gave products derived from 1- and 3-phenylpropynes and phenylallene. Methylation of the di- and tri-lithio-compounds followed by hydrolysis or silylation proved that attack occurs first at the benzylic carbon atom:

[MATHEMATICAL EXPRESSION NOT REPRODUCIBLE IN ASCII]

Allenic structures have been suggested for the di-, tri- and tetra-lithio-species on the basis of their i.r. spectra. Attempts to polylithiate the aliphatic ring of 1,2,3-triphenylcyclopropane resulted in ring opening, giving a mixture of stilbenes after hydrolysis.

The reaction of dilithiomethane with various boron and silicon halides gave compounds of the type R2BCH2BR2 and (Me3Si)2CH2. The former are not stable and dismute into BR3 and (RBCH2)n.

Functionally substituted organic compounds, such as nitriles and sulphones, easily form gem-dilithio-derivatives on treatment with excess n-butyl-lithium. Subsequent reactions occur only at the α-carbon atom, despite resonance stabilization:

[MATHEMATICAL EXPRESSION NOT REPRODUCIBLE IN ASCII]

Acetonitrile similarly gives the dilithio-compound Li2C2HN with t-butyl-lithium...

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We are committed to protecting the privacy and security of personal data. This policy tells you how we will collect and use your personal data, and what you should expect in respect of the personal information about you that we have collected.

We are PBShop.co.uk Limited (registered in England & Wales with Company No: 9366362). Our registered office is at Swatton Barn, Badbury, Swindon, SN4 0EU, United Kingdom.

The person with responsibility for our data protection compliance is the Managing Director and they can be contacted via email at help@pbshop.store.

We are the data controller of the personal data that we keep and use, and we are therefore responsible for making sure that our systems, processes and people comply with the relevant data protection laws in respect of that personal data.

We will act in respect of personal data to comply with the six principles of the General Data Protection Regulation (“GDPR”), which are:

Lawfulness, fairness and transparency;
Purpose limitation;
Data minimisation;
Accuracy;
Storage limitation;
Integrity and confidentiality.
You have rights in respect of how your personal data can be processed; these include the right to request:

a copy of your personal data;
that inaccurate data is rectified; and
that your personal data is, in certain circumstances, erased or restricted.
You have the right to complain to the Information Commissioner, which you can do by contacting the Information Commissioner’s Office (ICO) directly. Full contact details, including a helpline number, can be found on the ICO website (www.ico.org.uk). This website also has useful information on your rights and our obligations. However, please raise any concerns or issues with us first so that we may deal with this as quickly as possible for you.

COLLECTION, USE AND DISCLOSURE OF PERSONAL DATA
We collect and process data for the following reasons:

personal data collected and created in relation to our selling books and other items; and
personal data relating to our people (which means those people working for our company, or providing services to us, or potentially working or providing services to us, including employees, consultants, temporary or casual workers and contractors).
All of our people are required to abide by our Privacy Policy when handling personal data, and are provided with appropriate data protection training. Any breach of data protection will be taken seriously, and may result in disciplinary action.

Selling books and other items
COLLECTION:
We will collect personal information which may include names, addresses and other information for our customers. This will be done for the management of the commercial relationship with our customers.

We may collect this personal data from you directly, and also from third parties, including publicly available third party sources. Additional personal data will be collected as it is created by or supplied to us in the course of anything we do for you.

USE:
We will use the personal data in the course of making sales and to comply with requirements that we are required to undertake.

We will only use your personal data when the law allows us to. Most commonly, we will use your personal data in the following circumstances:

in performance of a contract (the agreement to sell books and other items); and/or
compliance with a legal obligation; and/or
vital interests of the data subject; and/or
where it is necessary for our legitimate interests (or those of a third party) and your interests and fundamental rights do not override those interests.
We may also use your personal data in the following situations, which are likely to be far less common:

where we need to protect your interests (or someone else’s interests);
where it is needed in the public interest or for official purposes.
DISCLOSURE:
We may share personal data with third parties as is necessary in the sale of books and other items, including to third party providers who deliver services to support the operation of our company.

In respect of all disclosures of personal data, we will only share the personal information which is necessary for the particular purpose for which it is provided, or where we have another legitimate interest in doing so, and we will ensure that the personal data is appropriately protected.

RETENTION PERIOD:
We will keep personal data only for as long as is necessary to fulfil the purposes for which we collected it, including for the purposes of satisfying any legal, accounting or reporting requirements. Normally, our retention period for personal data collected for this purpose is a minimum of 6 years after the end of the period that we are selling books and other items.

Our people
COLLECTION:
We will collect names, addresses, contact details, education and employment history, identity and other background checks (which may include appropriate criminal and financial checks and confirmation of the right to work in the UK), marital status and information on next of kin and dependents, financial information (such as bank details and NI numbers), date of birth, gender, a copy of your passport and driving licence, performance information and compensation history, recruitment information (including references), salary, benefits, pension and annual leave information, disciplinary and grievance information, photographs, information about your use of our information and communications systems and CCTV footage or other information obtained through electronic means.

We may collect and use special categories of personal data as required in the carrying out of obligations and exercising specific rights of us or the data subject in the field of employment. This may include information relating to matters such as health, racial origin, religious belief and offences or alleged offences.

Personal data may be collected from you during the selection process (for example via your application form and CV) and during your employment (including holiday forms, expense claims, performance reviews, any disciplinary or grievance processes), or from third parties, including referees, health service providers, background check providers.

USE:
Personal data of our people will be used for HR administration and management, both in respect of the selection of people to work for us (including suitability, eligibility and/or fitness to work), and those who do work for us, to include learning and development, disciplinary and security (of people, offices and data) requirements, providing and liaising with benefits providers, business management and planning (including accounting and auditing), paying you and dealing with tax and NI deductions, assessing and deciding on salary reviews and compensation, conducting performance reviews and managing performance, dealing with legal disputes involving you or others, preventing fraud, monitoring your use of our information and communications systems, ensuring compliance with our policies, and equal opportunities monitoring.

We will only use your personal data when the law allows us to. Most commonly, we will use your personal data in the following circumstances:

In performance of a contract with you; and/or
compliance with a legal obligation; and/or
vital interests of the data subject; and/or
where it is necessary for our legitimate interests (or those of a third party) and your interests and fundamental rights do not override those interests.
We may also use your personal data in the following situations, which are likely to be less common:

where we need to protect your interests (or someone else’s interests);
where it is needed in the public interest or for official purposes.
In respect of all disclosures of personal data, we will only share the personal information which is necessary for the particular purpose for which it is provided, or where we have another legitimate interest in doing so, and we will ensure that the personal data is appropriately protected.

In respect of special categories of personal data, we may process this in the following circumstances:

in limited circumstances with your explicit written consent; and/or
where we need to carry out our legal obligations and in line with our policies; and/or
where it is needed in the public interest (such as for equal opportunities monitoring or in relation to our occupational pension scheme), and in line with our policies; and/or
where it is needed to assess your working capacity on health grounds, subject to appropriate confidentiality safeguards.
Less commonly, we may process this type of information where it is needed in relation to legal claims or where it is needed to protect your (or someone else’s) interests and you are not capable of giving your consent, or where you have already made the information public. We may also process such information about our people (or former people) in the course of our legitimate business activities with the appropriate safeguards.

The special categories of personal data may be used in the following ways:

in relation to leaves of absence, to comply with employment and other laws;
in relation to your physical or mental health, or disability status, to ensure your health and safety in the workplace and to assess your fitness to work, to monitor, manage and administer benefits and absences;
in relation to your race, national or ethnic origin, religious, philosophical or moral beliefs, or your sexual life or sexual orientation, to ensure meaningful equal opportunity monitoring and reporting.
DISCLOSURE:
Personal data may be transferred to service providers who support the operation of our business (such as payroll service providers), to other third parties reasonably necessary in the conduct of our business (including insurers, professional advisors, regulators). These third parties may be acting as processor, or controller of personal data in their own right.

RETENTION PERIOD:
We will keep personal data only for as long as is necessary to fulfil the purposes for which we collected it, including for the purposes of satisfying any legal, accounting or reporting requirements. We will normally keep personal data of applicants who we do not employ for six months after we receive it.

We will keep personal data of employees throughout your employment and normally for a minimum of six years after your employment ends.

Changes to your personal data
It is very important that the personal information that we hold about you is accurate and current. Please tell us if your personal information changes during your relationship with us.

Data Security
We have put in place measures to prevent your personal data from being accidentally lost, used or accessed in an unauthorised way, altered or disclosed. In addition, we limit access to your personal data to those of our people and other third parties who have a business need to know. They will only process your personal data on our instructions and where they have agreed to treat the information confidentially and to keep it secure. We have put in place procedures to deal with any suspected data security breach and will notify you and the ICO of a suspected breach where we are legally required to do so.

Where we store your personal data
We principally store data, both electronically and on file, at our office.

Personal data may be transferred outside of the EEA by processors acting on our behalf. For transfers to countries not considered adequate by the EC, we will ensure that personal data is adequately protected, as required by the GDPR. This would include by use of the Standard Contractual Clauses adopted by the EC to protect personal data.

Your rights
Under certain circumstances, you have the right by law to request:

access to your personal data. This enables you to ask to receive a copy of the personal data that we hold about you and to check that we are lawfully processing it.
correction of the personal data that we hold about you.
erasure of your personal data.
object to processing of your personal data where we are relying on our legitimate interest and there is something about your particular situation which makes you want to object to processing on this ground. You also have the right to object where we are processing your personal information for direct marketing purposes.
restriction of processing of your personal data.
transfer of your personal data to another party.
Links from our website
Our website may, from time to time, contain links to and from the websites of third parties that we permit to make such links. If you follow a link to any of these websites, please note that these websites have their own privacy policies and that we do not accept any responsibility or liability for these policies. We recommend that you check these policies before you submit any personal data to these websites.

CHANGES TO THIS PRIVACY POLICY
Any changes we may make to our privacy policy in the future will be posted on our website, so please ensure that you are viewing the correct version.

Please contact us if you have any questions, comments or requests regarding this Privacy Policy.

Last amended May 2021.

Organometallic Chemistry

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