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Unusual Mode of Addition of 1,2‐Alkadienylidene Carbenes to 1,3‐Dienes: 1,4 Addition to Rigid and Flexible 1,3‐Dienes
Author(s) -
Sugita Hikaru,
Mizuno Kazuhiko,
Mori Toshiki,
Isagawa Kakuzo,
Otsuji Yoshio
Publication year - 1991
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.199109841
Subject(s) - carbene , yield (engineering) , diene , adduct , chemistry , medicinal chemistry , product (mathematics) , phase (matter) , organic chemistry , polymer chemistry , materials science , catalysis , mathematics , natural rubber , geometry , metallurgy
Surprisingly large amounts of the 1,4‐adducts 5 are formed in the reaction of 3,3‐diphenyl‐1,2‐propadienylidene ( 2 )—generated from 1 under phase‐transfer conditions—with the diene 3 . Compounds 4 and 5 (overall yield 37%) are formed in a ratio of 78 : 22. The overall yield and product ratio in such reactions are dependent on both the carbene and the diene.