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
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.