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Synthesis and Reactions of Isothiocyanate‐Substituted Allenes and 1,3‐Butadienes
Author(s) -
Banert Klaus,
Hückstädt Holger,
Vrobel Kai
Publication year - 1992
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.199200901
Subject(s) - isomerization , propargyl , cycloaddition , isothiocyanate , chemistry , nucleophile , sigmatropic reaction , allene , nucleophilic addition , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis
Unusually reactive towards nucleophiles are the allyl isothiocyanates 1 (R 1 , R 2 = H or Me), which can be prepared from the easily accessible propargyl thiocyanates by [3,3]‐sigmatropic shifts. Similar isomerization reactions also allow the preparation of 2 and 3 (R = H, Me). These compounds are suitable for the synthesis of heterocycles and for cycloaddition reactions.