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Organic Synthesis: The Disconnection Approach,9780471101611
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Organic Synthesis: The Disconnection Approach


Edition: 1st
Author(s): Stuart Warren (Cambridge Univ., UK)
ISBN10:  0471101613
ISBN13:  9780471101611
Format:  Paperback
Pub. Date:  1/1/1991
Publisher(s): WILEY

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SummaryTable of Contents
This book will help students to design their own organic synthesis, giving a wide coverage of synthetic methods. The disconnection approach is used throughout so that starting materials are chosen after analysing the structure of the target molecule. There are forty chapters: those on the synthesis of given types of molecule alternate with strategy chapters in which the methods just learnt are placed in a wider context. The instructional chapters cover many ways of making each type of molecule starting with simple aromatic and aliphatic compounds with one functional group and progressing to molecules with many functional groups. The number and position of these functional groups provides the classification for these chapters. The strategy chapters cover questions of selectivity, protection, and stereochemistry, and develop more advanced strategic thinking via reagents specially designed for difficult problems. Examples are drawn from pharmaceuticals, agrochemicals, natural products, pheromones, perfumery and flavouring compounds, dyestuffs, monomers, and intermediates used in more advanced synthetic work. Reasons for wishing to synthesise each compound are given, and further examples can be found in the accompanying workbook which also gives many problems and solutions classified in the same way as the main text. The book will also assist more experienced chemists who feel they are out of touch with present day thinking on the subject.

Workbook for Organic Synthesis: The Disconnection Approach The workbook which supports this text provides an extra selection of examples. Each example is analysed in the same way as those in the main text with disconnections followed by synthesis, allowing the student to explore a wider range of types of target molecule and synthetic method. The main function of the workbook is, however, to provide a graded series of problems which extend the student’s experience of the types of molecules being synthesised by organic chemists. These, together with the examples, are classified into the same 40 chapters as the main text so that it is possible to use them in conjunction with it. Each problem is followed by a suggested solution or solutions analysed in the same way as the examples and no methodology other than that introduced in the main text is required. Examples and problems are interspersed to provide a developing chain of argument.


A workbook providing additional examples, problems, and solutions for use with Warren's Organic Synthesis: The Disconnection Approach. Exercises correspond to chapters in the main text. Problems of special ease or difficulty are labeled for optional use. Workbook includes a formula index of all target molecules contained in the text and workbook.
Introduction xi
The Disconnection Approach
1(5)
Basic Principles: Synthesis of Aromatic Compounds
6(10)
Strategy I: The Order of Events
16(10)
One-Group C-X Disconnections
26(8)
Strategy II: Chemoselectivity
34(7)
Two-Group C-X Disconnections
41(10)
Strategy III: Reversal of Polarity, Cyclisation Reactions, Summary of Strategy
51(9)
Amine Synthesis
60(6)
Strategy IV: Protecting Groups
66(9)
One-Group C-C Disconnections I: Alcohols
75(11)
General Strategy A: Choosing a Disconnection
86(7)
Strategy V: Stereoselectivity A
93(13)
One-Group C-C Disconnections II: Carbonyl Compounds
106(8)
Strategy VI: Regioselectivity
114(5)
Alkene Synthesis
119(7)
Strategy VII: Use of Acetylenes
126(6)
Two-Group Disconnections I: Diels-Alder Reactions
132(8)
Strategy VIII: Introduction to Carbonyl Condensations
140(4)
Two-Group Disconnections II: 1,3-Difunctionalised Compounds and α,β-unsaturated Carbonyl Compounds
144(8)
Strategy IX: Control in Carbonyl Condensations
152(18)
Two-Group Disconnections III: 1,5-Difunctionalised Compounds, Michael Addition and Robinson Annelation
170(9)
Strategy X: Use of Aliphatic Nitro Compounds in Synthesis
179(6)
Two-Group Disconnections IV: 1,2-Difunctionalised Compounds
185(12)
Strategy XI: Radical Reactions in Synthesis. FGA and its Reverse
197(12)
Two-Group Disconnections V: 1,4-Difunctionalised Compounds
209(8)
Strategy XII: Reconnections
217(6)
Two-Group Disconnections VI: 1,6-Difunctionalised Compounds
223(6)
General Strategy B: Strategy of Carbonyl Disconnections
229(11)
Strategy XIII: Introduction to Ring Synthesis. Saturated Heterocycles
240(11)
Three-Membered Rings
251(8)
Strategy XIV: Rearrangements in Synthesis
259(9)
Four-Membered Rings: Photochemistry in Synthesis
268(6)
Strategy XV: Use of Ketenes in Synthesis
274(4)
Five-Membered Rings
278(5)
Strategy XVI: Pericyclic Rearrangements in Synthesis Special Methods for Five-Membered Rings
283(9)
Six-Membered Rings
292(9)
General Strategy C: Strategy of Ring Synthesis
301(13)
Strategy XVII: Stereoselectivity B
314(12)
Aromatic Heterocycles
326(20)
General Strategy D: Advanced Strategy
346(20)
General References 366(1)
References 367(14)
Index 381

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