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Ring‐opening isomerization addition reaction of bicyclo ortho esters with acid chlorides. Model reaction for development of a novel polyaddition reaction accompanying ring‐opening isomerization
Author(s) -
Nishida Haruo,
Sanda Fumio,
Endo Takeshi,
Nakahara Takeshi,
Ogata Takayuki,
Kusumoto Koshi
Publication year - 1999
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19990401)200:4<745::aid-macp745>3.0.co;2-r
Subject(s) - isomerization , chemistry , chloride , ring (chemistry) , bicyclic molecule , benzoyl chloride , polymer chemistry , reaction mechanism , photochemistry , medicinal chemistry , organic chemistry , catalysis
The reaction of bicyclo ortho esters (BOEs) with acid chlorides was examined. The BOEs readily reacted with acid chlorides to give the corresponding adducts via ring‐opening isomerization. The order of the reactivities of the acid chlorides is as follows, sebacoyl chloride ⪈ adipoyl chloride > succinyl chloride and 1,3,5‐benzenetricarbonyl chloride > isophthaloyl chloride ⪈ benzoyl chloride. It is considered that the ring‐opening isomerization of the BOEs with acid chlorides proceeds by a similar mechanism as that of the homopolymerization of the BOEs.