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Paternò–Büchi photochemical [2 + 2] cycloaddition of aromatic carbonyl compounds with 2‐siloxy‐1 H ‐pyrrole derivatives
Author(s) -
Xue Jianfei,
Abe Manabu,
Takagi Ryukichi
Publication year - 2017
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3632
Subject(s) - regioselectivity , chemistry , oxetane , benzophenone , pyrrole , cycloaddition , bicyclic molecule , medicinal chemistry , photochemistry , stereochemistry , organic chemistry , catalysis
The purpose of this study was to explore regioselectivity and stereoselectivity in the Paternò–Büchi reaction of pyrrole derivatives. The regioselective formation of a bicyclic oxetane in the Paternò–Büchi reaction of 2‐siloxypyrrole with benzophenone was reported for the first time, and a mechanism involving the distribution of the intermediary triplet diradicals was proposed to account for the regioselectivity of the reaction. Copyright © 2016 John Wiley & Sons, Ltd.