Houben-Weyl Guide

Introduction

Houben-Weyl Methods of Organic Chemistry was founded in 1909 and has had the goal of providing a comprehensive description of preparative methods, organized on the basis of the product functional group and the types of bonds made in building up that functionality. All known synthetic methods leading to a given product class are covered in the individual volumes, usually followed by a concise overview of the reactions of that compound class.

The 4th Edition was published between 1952 and 1986 and consisted of 67 volumes comprising 67 individual books and 3 index volumes. The series was updated with 89 additional and supplemental volumes published between 1982 and 2001. The 4th Edition and Supplemental Volumes are an invaluable reference source for the synthetic chemist, because they present a comprehensive, critical evaluation of all the literature from the very beginning, whether published in primary, secondary or patent sources.

The purpose of this guide is to provide the synthetic chemist with rapid access to the synthetic methods contained in the 156 volumes of the 4th Edition and Supplemental Series. The systematic organizational principles of Houben-Weyl simplify this task, since they complement retrosynthetic analysis. You need only identify the functional group or structural unity you want to build up. Then find that system in the General Chart (p 6), which is organized from left to right according to the number of heteroatoms bound to carbon and from top to bottom according to the total number of sigma and pi bonds to these heteroatoms. This classification system, which has been used in Houben-Weyl from the first edition, corresponds to the general notion of oxidation state.

The General Chart (p 6) will refer you to the location of your target functionality in the Fine Chart, where you will be directed to the volume in which your system is covered. The final step is to go to the table of contents of the volume in question to locate the pages on which your system is covered.

If your target molecule contains several functionalities or structural units, only the one you want to build up is relevant. If you want to prepare two functionalities simultaneously, then you have to look under both.

Several volumes of Houben-Weyl deal with important areas not otherwise treated in a focused way: Stereoselective Synthesis, Peptides, Polymers, etc. If you have a synthetic problem related to one of these areas, you should go directly to the table of contents of the appropriate volume.

That means:

1. First you have to clear up which Bond or Bonds you want to build up; for instance:

2. Then you have to clear up the surroundings round about the C- or X-Atom; for instance:

3. After that you have a look at the General Chart (p. 6) to find your system (compound class):

4. Have you found your compound class, then you have the page Number of the Fine Chart. The Fine Chart gives you the Vol.-Number of the E-Series first and then underneeth of the 4th Edition or of a special Vol. of the E Series.

Have you the Volume, than you can directly go into the contents (see Vol. E 23 n and o).

5. Do you want the simultaneous synthesis of two Functions; for instance

you have to look under both Functions:

6. Some Vol. involved with special problems (p. 6, 18 f.); for instance:

Stereoselective synthesis

Photochemistry

Peptides (including Chemistry of Protecting Groups)

Polymers (including Cellulose)

etc.