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Azo bridges from azines, XVI . 1,2,3‐oxadiazolidines by intramolecular [3 + 2] cycloaddition
Author(s) -
Hünig Siegfried,
Schmitt Michael
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199510252
Subject(s) - chemistry , cycloaddition , moiety , intramolecular force , azoxy , norbornene , double bond , stereochemistry , medicinal chemistry , catalysis , polymer chemistry , organic chemistry , polymer , polymerization
Olefinic bonds and an azoxy group held in a rigid parallel position in systems of type I undergo smooth thermal [3 + 2] cycloadditions which can be strongly catalyzed by acids. Double bonds of a bicycloheptene (norbornene) moiety are ca. 10 times more reactive than those of a bicyclooctene system. The newly formed cage compounds of type K are the first stable derivatives of the so far unknown 1,2,3‐oxadiazolidine.