MARCH'S ADVANCED ORGANIC CHEMISTRY:

Abstract

Knowledge of organic chemistry continues to move ahead on many fronts. New journals continue to appear and older ones increase in frequency of publication and/or in number of papers published. This Fifth Edition of Advanced Organic- Chemistry has been thoroughly revised to reflect this growth. Every topic retained from the fourth edition has been brought up to date. Changes, ranging from minor to extensive, have been made on virtually every page of the Fifth Edition. More than 2800 new references have been added. Several older references were deleted and in cases where a series of papers by the same principal author were cited, all but the most recent were deleted. The older citations should be found in the more recent one or ones. A few changes were made in the organization, but the structure of the Fifth Edition is essentially the same as that of all previous ones. A total of 41 new sections were added, and 54 old ones were deleted. In most cases, the information from the deleted sections was combined with others or moved to another section. The new sections reflect new aspects of organic chemistry. Representative examples include 10-20 (hydroxylation of silanes), 15-36 (radical cyclization), 15-47 (dihydroxylation of aromatic rings), and 19-15 (oxidation of methylene to OH, O2CR, or OR). In some cases, old sections were split to reflect modern applications. Representative examples are the Diels-Alder reaction (split into the normal reaction and heteroatom Diels-Alder reactions; 15-58 and 15-59); the aldol and the Mukaiyama aldol reaction (16-38 and 16-39); and the reaction of organometallic reagents with alkyl halides (10-94 for Group I and II metals, 10-95 for organocuprates, and 10-96 for other metal reagents). Like the first four editions, this edition is intended to be a textbook for a course in advanced organic chemistry taken by students who have had the standard undergraduate organic and physical chemistry courses. The goal, as in previous editions, is to give equal weight to the three fundamental aspects of the study of organic chemistry: reactions, mechanisms, and structure. A student who has completed a course based on this book should be able to approach the literature directly, with a sound knowledge of modern basic organic chemistry. Major special areas of organic chemistry (terpenes, carbohydrates, proteins, many organometallic reagents, combinatorial chemistry, polymerization and electrochemical reactions, steroids, etc.) have been treated lightly or ignored completely. I share Professor March's opinion that these topics are best approached after the first year of graduate study, when the fundamentals have been mastered, either in advanced courses, or directly, by consulting the many excellent books and review articles available on these subjects. In addition, many of these topics are so vast, they are beyond the scope of this book.