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The Synthetic Potential of the Isocyanide‐Cyanide Rearrangement
Author(s) -
Meier Michael,
Rüchardt Christoph
Publication year - 1987
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19871200102
Subject(s) - chemistry , isocyanide , synthon , cyanide , isomerization , thermal decomposition , allylic rearrangement , optically active , medicinal chemistry , photochemistry , organic chemistry , catalysis
Excellent chemical and optical yields (>96% retention) of cyanides are achieved by vapor phase thermolysis or short contact flow thermolysis of isocyanides. trans ‐2‐Butenyl isocyanide rear‐ranges without concomitant allylic isomerization to trans ‐2‐butenyl cyanide. Optically active 1‐(formyloxymethyl)‐2‐phenylethyl cyanide is obtained from optically active L ‐phenylalanine as a new type of chiral pool synthon.