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Photoinduced Cyclization of ( o ‐Alkylbenzoyl)phosphonates to Benzocyclobutenols
Author(s) -
Ishida Naoki,
Yano Takaaki,
Yuhki Tatsuya,
Murakami Masahiro
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700766
Subject(s) - phosphonate , substituent , reversion , chemistry , ring (chemistry) , irradiation , character (mathematics) , stereochemistry , closing (real estate) , photochemistry , organic chemistry , physics , mathematics , biochemistry , geometry , political science , nuclear physics , law , gene , phenotype
( 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.