ONE-STEP CONVERSION OF HIGHLY DIPOLAROPHILIC OLEFINS TO ALPHA-HYDROXY-BETA-CYANOADDUCTS WITH METAL FULMINATE

Authors
YOU ZQ LEE HJ
Citation
Zq. You et Hj. Lee, ONE-STEP CONVERSION OF HIGHLY DIPOLAROPHILIC OLEFINS TO ALPHA-HYDROXY-BETA-CYANOADDUCTS WITH METAL FULMINATE, Tetrahedron letters, 37(8), 1996, pp. 1165-1168
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
8
Year of publication
1996
Pages
1165 - 1168
Database
ISI
SICI code
0040-4039(1996)37:8<1165:OCOHDO>2.0.ZU;2-A
Abstract
Olefins conjugated with carbonyl, carboxylic ester, and phenyl;groups as well as highly strained non-conjugated olefin norbornylene were con verted to their corresponding alpha-hydroxy-beta-cyanoadducts by treat ment with mercuric fulminate and lithium bromide. The transformation a ppears to go through a 1,3-dipolar cycloaddition of metal fulminate to the olefin followed by a spontaneous cleavage of the resulting hetero cycle. Thus, the study provides the first one step cis-cyanohydroxylat ion of olefinic species.