Fundamentals of Medicinal Chemistry

Table 10.2 Examples of books and databases that catalogue chemical reactions

Title Author Classification used

Books:

Synthetic Organic Chemistry Wagner and Zook Lists reactions according to the

functional group being produced.

Organic Functional Group

Preparations.

Sandler and Karo Lists reactions according to the

functional group being produced.

Oxidations in Organic Chemistry Hudlicky Lists and discusses

transformations that can be

brought about by oxidation.

Reduction in Organic Chemistry Hudlicky Lists and discusses

transformations that can be

brought about by reduction.

Databases:

CASREACT The Chemical Abstracts

Research Service

Information from 1985. Covers

single and multistep reactions.

Includes CAS Registry numbers of

reactants, products, reagents,

catalysts and solvents. It is

structure searchable.

ISI Reaction Centre Institute for Scientific

Information

Data from 1840. Classified

according to reaction type.

Includes biological assays.

Crossfire Beilstein Information

Service

Three main types of data,

structural and properties,

reactions including preparations

and chemical literature references.

Z Z

+

CH 2

+ H 2 C

Free radicals

(a)

.

R^1 R

1

R^1 R^1

R^2

R^2

R^2

R^2

CH 2

+ H 2 C

_

+

Electrophile Nucleophile

(b) (c)

Z = An electron withdrawing group

.

Figure 10.11 (a) Homolytic, (b) heterolytic and (c) pericyclic bond disconnections. Homolytic

disconnections are usually disregarded because it is difficult to predict the outcome of reconnec-

tion reactions

This is because theydivide themolecule into electrophilicand nucleophilic species,

which can be more easily converted into the appropriate electrophilic and nucleo-

philic reagents for reconnection. The most useful heterolytic disconnections are

DESIGNING ORGANIC SYNTHESES 215