✦ LIBER ✦

The exo-Outstretching Effect Governing the Exclusive Stereoselectivity of the Intramolecular [2+2] Photocycloaddition of Vinylarenes

✍ Scribed by Jun Nishimura; Takashi Funaki; Noriaki Saito; Seiichi Inokuma; Yosuke Nakamura; So Tajima; Toshitada Yoshihara; Seiji Tobita

Publisher: John Wiley and Sons
Year: 2005
Tongue: German
Weight: 334 KB
Volume: 88
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200590103

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✦ Synopsis

Abstract

Intramolecular [2+2] photocycloaddition of a dimeric vinylpyridine 1 through a singlet‐excited species efficiently formed the corresponding syn‐ and anti‐pyridinophanes 2 and 3. The syn‐isomers were elucidated spectroscopically and by X‐ray crystallography as exo,syn‐configured. The high selectivity under formation of exo,syn‐2 was thoroughly investigated. Consequently, an exo‐outstretching effect, which is observed around the periphery of a face‐to‐face‐oriented system between two aromatic nuclei as a transition state, on cyclobutane ring formation was discovered for the first time.

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