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Photocycloaddition of Some Difluoro(aminoenonato)boron Complexes with Arylalkenes

✍ Scribed by Kuniaki Itoh; Kazuhiko Okazaki; Yuan L. Chow

Book ID
102257199
Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
135 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The photocycloaddition of some difluoro[(methylamino‐κN)alkenonato‐κO]boron complexes 1 with arylalkenes 2 is discussed. The resulting [2+2] photoaddition gave the cyclobutane and azetidine derivatives (Schemes 1, 3, and 5). Rearrangements of the cyclobutane gave 1,5‐diketones derivatives (Schemes 2, 4, and 5). The yields of the photoadducts were governed by the reduction and oxidation potentials. Furthermore, the configurations of the products established high regio‐ and stereoselectivity, suggesting the presence of a singlet exciplex. The reactivity and the stereochemistry were rationalized by means of FMO (frontier molecular orbital) calculations.

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