3 years ago

Photoinduced Cyclization of (o-Alkylbenzoyl)phosphonates to Benzocyclobutenols

Photoinduced Cyclization of (o-Alkylbenzoyl)phosphonates to Benzocyclobutenols
Masahiro Murakami, Takaaki Yano, Naoki Ishida, Tatsuya Yuhki
(o-Alkylbenzoyl)phosphonates readily cyclize to highly strained benzocyclobutenols simply upon irradiation with UV light. The remarkable efficiency is ascribed to the electron-accepting character of the phosphonate substituent, which facilitates thermal ring closing of the o-quinodimethane intermediate and suppresses reversion to the starting carbonyl compound. Afraid of sunlight? (o-Alkylbenzoyl)phosphonates readily cyclize to highly strained benzocyclobutenols simply upon irradiation with UV light. Mechanistic studies suggest that the electron-accepting character of the phosphonate substituent leads to remarkable efficiency.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/asia.201700766

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