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[2 + 2]‐Cycloaddition of a Vinyl Cation
Author(s) -
Hammen Günter,
Hanack Michael
Publication year - 1979
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197906142
Subject(s) - solvolysis , cycloaddition , nucleophile , chemistry , cyclohexene , character (mathematics) , ion , organic chemistry , medicinal chemistry , polymer chemistry , hydrolysis , catalysis , mathematics , geometry
The first cycloaddition to a vinyl catoin has now been accomplished: (2) , obtained from (1) by solvolysis in the presence of AgBF 4 , reacts with cyclohexene to give mainly the cation (3) and thence to (4) . In contrast, reaction with F 3 CCOOAg gives only the ester [ (1) , F 3 CCOO in place of Br]; the pronounced nucleophilic character of the trifluoroacetate ion prevents cycloadditon (An = p ‐methoxyphenyl).