Photochemical Key Steps in Organic Synthesis

Authored by: Norbert Hoffmann

CRC Handbook of Organic Photochemistry and Photobiology

Print publication date:  March  2012
Online publication date:  March  2012

Print ISBN: 9781439899335
eBook ISBN: 9781466561250
Adobe ISBN:

10.1201/b12252-6

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Abstract

Photochemical reactions are characterized by the transformation of electronically excited molecules that are generated by light absorption. 1,2 Compared to their ground state, such excited molecules possess completely different electronic configurations. Consequently, their chemical reactivity completely changes. Frequently, complementary reactions are observed for molecules at the ground and the excited states. 3 Thus, using photochemical reactions, the spectrum of chemical transformations of a compound family is significantly enlarged. Total syntheses can be shortened, and frequently complex, polycyclic, or highly functionalized structures can easily be obtained from simple substrates. 4 New product families or product libraries difficult to achieve with ground-state reactions are thus available, opening new perspectives in the search of biologically active compounds. Catalytic reactions are also affected by light irradiation. Either ground-state reactions become more efficient or new catalytic reactions are observed. Such reactions also enrich the methodology in organic synthesis. After a period of stagnation, activity in the field of organic photochemical reactions and their application to synthesis has started to grow again in academic and industrial research. In the two preceding editions of this handbook 5 as well as in other books, 1,6,7 large collections of organic photochemical reactions are presented. Many books deal with experimental conditions and equipment. 1,8 This chapter briefly discusses some selected examples predominantly chosen in the field of total synthesis and synthesis of biologically active compounds. The examples have been manly taken from recent literature.

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