O-NITROPHENYL SELENOCYANATE, A VALUABLE REAGENT IN ORGANIC-SYNTHESIS - APPLICATION TO ONE OF THE MOST POWERFUL ROUTES TO TERMINAL OLEFINS FROM PRIM-ALCOHOLS (THE GRIECO-SHARPLESS OLEFINATION REACTION) AND TO THE REGIOSELECTIVE ISOMERIZATION OF ALLYL ALCOHOLS

Authors
KRIEF A LAVAL AM
Citation
A. Krief et Am. Laval, O-NITROPHENYL SELENOCYANATE, A VALUABLE REAGENT IN ORGANIC-SYNTHESIS - APPLICATION TO ONE OF THE MOST POWERFUL ROUTES TO TERMINAL OLEFINS FROM PRIM-ALCOHOLS (THE GRIECO-SHARPLESS OLEFINATION REACTION) AND TO THE REGIOSELECTIVE ISOMERIZATION OF ALLYL ALCOHOLS, Bulletin de la Societe chimique de France, 134(10-11), 1997, pp. 869-874
Citations number
65
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
134
Issue
10-11
Year of publication
1997
Pages
869 - 874
Database
ISI
SICI code
0037-8968(1997)134:10-11<869:OSAVRI>2.0.ZU;2-2
Abstract
o-Nitrophenyl selenocyanate allows the transformation, in neutral medi a, of alcohols into o-nitrophenyl selenides (the Grieco reaction). On oxidation, alkyl o-nitrophenyl selenides produce olefins (the Sharples s olefination reaction) whereas allylic compounds undergo a smooth [2, 3] sigmatropic shift that leads to 'rearranged' allyl alcohols. Becaus e of its mildness, efficiency and chemoselectivity, the olefination re action has proved to be the best method so far described for the synth esis of terminal C,C double bonds from primary alcohols (the Grieco-Sh arpless reaction).