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 isomerisation of allyl alcohols | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

4147105

Reference Type

Journal Article

Title

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 isomerisation of allyl alcohols

Author(s)

Krief, A; Laval, AM

Year

1997

Is Peer Reviewed?

Yes

Journal

Bulletin de la Société Chimique de Paris
ISSN: 0037-8968

Volume

134

Issue

10-11

Page Numbers

869-874

Web of Science Id

WOS:000073962100005

Abstract

o-Nitrophenyl selenocyanate allows the transformation, in neutral media, of alcohols into o-nitrophenyl selenides (the Grieco reaction). On oxidation, alkyl o-nitrophenyl selenides produce olefins (the Sharpless olefination reaction) whereas allylic compounds undergo a smooth [2,3] sigmatropic shift that leads to 'rearranged' allyl alcohols. Because of its mildness, efficiency and chemoselectivity, the olefination reaction has proved to be the best method so far described for the synthesis of terminal C,C double bonds from primary alcohols (the Grieco-Sharpless reaction).

Keywords

alcohol; alkyl selenide; olefin synthesis; oxidation; selenoxide; allyl selenide; [2,3] sigmatropic rearrangement; allyl alcohol synthesis