Organic Synthesis: The Disconnection Approach

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Organic Synthesis: The Disconnection Approach

  • by Stuart Warren
  • Filetype: pdf
  • Filesize: 36.31 MB
  • Language: English





  • Publisher:   Wiley
  • Number Of Pages:   404
  • Publication Date:   1984-02
  • Sales Rank:   168538
  • ISBN / ASIN:   0471101613
  • EAN:   9780471101611
  • Binding:   Paperback
  • Manufacturer:   Wiley
  • Studio:   Wiley
  • Average Rating:   4.5
  • Total Reviews:   5


Book Description:

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.


Date: 2006-02-25   Rating: 3

good, but a bit dated

This is the first and only edition of this book, which, while it explains all the theory behind retrosynthesis quite well, is a bit lacking in some of the techniques that have (I presume) been discovered since it was published some 25 years ago. It's mostly there, but just make sure you consult some different sources for specific things, like 1,4 relationships (there's no mention of 1,3-dithianes at all in this book). All in all though, a thorough and reasonably accessible treatment of the topic.

Date: 2002-03-07   Rating: 5

Retrosynthetic Analysis

Warren's Organic Synthesis-Disconnection Approach focuses on retrosynthetic analysis in organic synthesis. Some of the central concepts introduced in this strategy book are synthons, target molecule, FGI (functional group interconversion), disconnection, and reagent.

Synthons: an idealized fragment, usually a cation or an anion, resulting from a disconnection. Synthons may or may not be an intermediate in the corresponding reaction.

Disconnection: the reverse operation to a reaction. The imagined cleavage of a bond to "break" the molecule into possible starting materials.

Functional group interconversion: the process of converting one functional group into another by substitution, addition, elimination, oxidation, or reduction, and the reverse operation used in retrosynthetic analysis.

Reagent: Warren introduces a formal and rigid definition of reagent in this book. Reagent is a compound used in practice for a synthon.

Warren's treatise of organic synthesis emphasizes visualizing and choosing not only the most obvious but the most efficient disconnection (retrosynthesis) in synthesizing a target molecule. The book is set up in a fashion such that synthetic strategies and organic reactions are presented in alternating chapters. Strategies aim to enforce tricks and concepts of organic synthesis like stereoselectivity, control of regiochemistry and stereochemistry, control of carbonyl condensation, order of events in synthesis, rearrangements, use of ringed molecules. Reaction chapters present some of the most significant reactions in organic synthesis, with an emphasis of those involve carbon-carbon formation.

Topics of Warren's Organic Synthesis:
Synthesis Strategies
-The Disconnection Approach
-The Order of Events
-Reversal of Polarity, Cyclization Reactions
-Protecting Groups
-Choosing a Disconnection (General Strategy)
-Use of Acetylenes
-Introduction of Carbonyl Condensations
-Control in Carbonyl Condensations
-Use of Aliphatic Nitro Compounds in Synthesis
-Radical Reactions in Synthesis
-Introduction to Ring Synthesis, Saturated Heterocycles
-Rearrangements in Synthesis
-Use of Ketenes in Synthesis
-Pericyclic Rearrangements in Synthesis
-Special Methods for 5-Membered Rings

Reaction Methods
-One Group C-X Disconnections
-Two Group C-X Disconnections
-Amine Synthesis
-One Group C-C Disconnections: Alcohols
-One Group C-C Disconnections: Carbonyl Compounds
-Alkene Synthesis
-Two Group Disconnections: Diels-Alder Reactions
-Two Group Disconnections: 1,3-Difunctionalized Compounds and alpha,beta-unsaturated Carbonyl Compounds
-Two Group Disconnections: 1,5-Difunctionalized Compounds, Michael Addition, Robinson Annulation
-Two Group Disconnections: 1,2-Difunctionalized Compounds
-Two Group Disconnections: 1,4-Difunctionalized Compounds
-Two Group Disconnections: 1,6-Difunctionalized Compounds
-Three-Membered Rings
-Four-Membered Rings: Photochemistry in Synthesis
-Five-Membered Rings
-Six-Membered Rings
-Aromatic Heterocycles

The book teaches retrosynthetic analysis in organic synthesis. The ability to recognize an obvious and/or obscure disconnection facilitates organic synthesis tremendously. The methods and strategies presented in Warren gives advanced undergraduate students, graduate students and practicing chemists an overview of the most significant retrosynthetic pathways. Exceptional work.

Date: 2000-08-15   Rating: 5

Retrosynthesis Primer

The book treats the subject of organic retrosynthesis in a very clear fashion. It will be a perfect companion for students taking sunthetic organic chemistry course.

Date: 2000-01-03   Rating: 5

Great way to learn organic synthesis!

I am a grad student in a Top10 univ in US. I found Dr Warrens book an useful guide for the retrosynthtic approach to learning organic chemistry. A "must have" book..

Date: 1998-02-10   Rating: 5

Thinking about synthesis

Gets your mind thinking in the best way to make compounds. Instead of trying to remember hundreds of transformations, Warren's book shows you how to disconnect the compound into is smallest parts and how they could be put together. Basically, he discribes how to do retro-synthesis. Certainly another must for any medicinal or organic chemist.