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Oxetane formation by addition of N ‐substituted imidazoles to benzophenone and poly(4‐vinylbenzophenone)s
Author(s) -
Ito Yoshikatsu,
Kusunaga Yoshitaka,
Tabata Kenichi,
Arai Hitoshi,
Meng JiBen,
Matsuura Teruo
Publication year - 1993
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1993.070501117
Subject(s) - oxetane , benzophenone , chemistry , photochemistry , intramolecular force , styrene , polymer chemistry , ring (chemistry) , imidazole , copolymer , stereochemistry , organic chemistry , polymer
Abstract Photochemical oxetane formation by addition of 1‐methyl‐2,4,5‐triphenylimidazole ( 1a ), 1,2‐dimethyl‐4,5‐diphenylimidazole ( 1b ), and 1‐acetylimidazole ( 1c ) to benzophenone (BP), poly(4‐vinylbenzophenone) (PVBP), and poly(styrene‐ co ‐4‐vinylbenzophenone) (PSVBP) was studied in the solution and solid phases. In solution, BP underwent the photoaddition smoothly to all three imidazoles 1a–1c . On the other hand, the photoaddition of PVBP and PSVBP depended on the imidazole employed, that is, 1b and 1c produced the corresponding oxetane, but 1a did not. The lack of oxetane formation from the polymeric BP and 1a is probably due to a rapid triplet‐sensitized decomposition of a once‐formed oxetane ring as a result of the intramolecular triplet energy transfer from a pendant benzophenone group. © 1993 John Wiley & Sons, Inc.