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Photocycloaddition of Some Difluoro(aminoenonato)boron Complexes with Arylalkenes
Author(s) -
Itoh Kuniaki,
Okazaki Kazuhiko,
Chow Yuan L.
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490027
Subject(s) - chemistry , cyclobutane , azetidine , boron , stereoselectivity , reactivity (psychology) , singlet state , molecular orbital , stereochemistry , photochemistry , medicinal chemistry , computational chemistry , molecule , organic chemistry , ring (chemistry) , catalysis , excited state , pathology , nuclear physics , medicine , physics , alternative medicine
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.