Author(s): Malcolm Sainsbury
Publisher: Elsevier
Date : 1995
Pages : 382
Format : PDF
OCR : Y
Quality :
Language : English
ISBN-10 : 0444822429
ISBN-13 :
Second Supplements to the 2nd Edition of Rodd's Chemistry of Carbon Compounds : Aromatic Compounds : Part B: Benzoquinones and Related Compounds: Derivatives ... and Phenolic Aralkyl Compounds,
By Malcolm Sainsbury
* Publisher: Elsevier Publishing Company
* Number Of Pages: 382
* Publication Date: 1995-08-01
* ISBN-10 / ASIN: 0444822429
* ISBN-13 / EAN: 9780444822420
This volume spans several very important areas of aromatic chemistry. It
includes chapters devoted to benzoquinone, nitro compounds, metallo derivatives
and aromatic hydrocarbons with substituents which contain more than
one nitrogen atom, e.g., azobenzenes, azides, etc.
The first chapter is written by Dr. Malcolm Bruce. It is fitting that I should
recognise Dr. Bruce's special contribution to Rodd, since it was he who wrote
on this subject in the 2nd edition in 1974 and again in the 1st Supplement.
Dr. Bruce's enthusiasm and lifelong interest in this subject is still very evident,
and this can easily be judged by the style with which he has surveyed progress
in benzoquinone chemistry in the last decade.
The application of organometallic chemistry to synthesis has been spectacular,
and two chapters in this volume emphasise this development. With so
much information, the task of condensing the most significant new knowledge
into a readable and informative account is a daunting one. Yet the authors,
Dr. Mullins and Professors Pearson and Woodgate, have managed this with
skill and flair. Dr. Simon Fortt has written on the chemistry of the nitroarenes.
This is a subject steeped in history, but it is still very much alive and relevant
today as is highlighted in Dr. Fortt's contribution.
I would like to thank all the authors for making my job as editor an easy
and intellectually rewarding one.
Malcolm Sainsbury Bath
March 1995
Contents
Volume III B/C/D (partial)
ix
Aromatic Compounds: Benzoquinones and related compounds: Derivatives of mononuclear
benzenoid hydrocarbons with nuclear substituents attached through an element
other than the non-metals in Groups VI and VII of the Periodic Table
Nuclear-substituted benzenoid hydrocarbons with more than one nitrogen atom in a
substituent group
Monobenzenoid and phenolic aralkyl compounds, their derivatives and oxidation products:
Depsides, tannins, lignans, lignin and humic acid
List of contributors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . vi
Preface . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . vii
List of common abbreviations and symbols used . . . . . . . . . . . . . . . . . . . . . . . . xiii
Chapter 8. Benzoquinones and Related Compounds
by J. MALCOLM BRUCE
1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
2. Bibliography . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2
3. Overview of quinone reactivity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
(a) Electron transfer . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
(b) Addition of nucleophiles . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
(c) Cycloaddition reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14
(d) Substitution reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 20
(e) Photochemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
(f) Complexes and molecular assemblies . . . . . . . . . . . . . . . . . . . . . . . . . . 25
(g) Ring fragmentation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
4. Synthesis of benzoquinones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 29
(a) From phenols and hydroquinones and their ethers . . . . . . . . . . . . . . . . 29
(b) From cyclobutene-1, 2-diones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31
5. Benzoquinone methides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35
(a) Overview of quinone methide reactivity . . . . . . . . . . . . . . . . . . . . . . . . . 35
(b) 1,2-Benzoquinone methides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36
(c) 1, 4-Benzoquinone methides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42
6. Thiobenzoquinones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 45
7. Benzoquinone imines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46
(a) 1, 2-Benzoquinone imines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46
(b) 1, 4-Benzoquinone imines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47
8. Homobenzoquinones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48
9. Benzoquinols (hydroxycyclohexadienones) . . . . . . . . . . . . . . . . . . . . . . . . . . 49
(a) 1, 4-Benzoquinols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 50
(b) 1, 2-Benzoquinols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 52
(c) 1, 4-Benzoquinol imines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53
Chapter 9. Derivatives of Benzenoid Hydrocarbons with Substituents
containing a single Nitrogen Atom
by S.M. FORTT
1. Nitro derivatives of benzene, its homologues and other substituted benzenes 55
(a) Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55
(b) Oxidation of aromatic amines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59
(c) Properties and reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60
2. Nitroso derivatives of benzene and its homologues . . . . . . . . . . . . . . . . . . . 64
(a) Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64
(b) Properties and reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 65
3. N-Arylhydroxylamines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66
(a) Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66
(b) Properties and reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67
4. N-Arylnitrones and N-arylnitroxides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69
5. Aromatic amines derived from benzene and its homologues nuclear primary
monoamines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 70
(a) Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 70
(b) Properties and reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 74
6. Benzenediamines and benzenetriamines . . . . . . . . . . . . . . . . . . . . . . . . . . . 76
(a) Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 76
(b) Properties and reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
7. N-Substituted arylamines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 78
(a) Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 78
(b) Properties and reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 83
8. N-Arylamides 84
(a) Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8
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