[2 + 2]‐Cycloaddition of a Vinyl Cation | Zendy

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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).

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