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Regio- and stereoselective .gamma. substitution of allylic alcohols with alkyllithium compounds by using N,N-methylphenylaminotributylphosphonium iodide. Anti stereochemistry of SN2' reaction

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This article is published in Journal of the American Chemical Society.The article was published on 1978-07-01. It has received 32 citations till now. The article focuses on the topics: Allylic rearrangement & SN2 reaction.

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Nucleophilic and organometallic displacement reactions of allylic compounds: stereo-and regiochemistry

TL;DR: In this paper, stereo and regiochemical aspects of three reaction types: the SN2' reaction (bimolecular nucleophilic substitution with allylic rearrangement); displacement reactions effected by organometallic reagents; the conversion of allylic alcohols into halides.
Journal ArticleDOI

d-Orbital stereoelectronic control of the stereochemistry of SN2' displacements by organocuprate reagents

TL;DR: In this paper, the anti-stereochemistry observed in organocuprate SN2′ displacements can be rationalized as a stereoelectronic effect arising from bidentate binding involving a d orbital of nueleophilic copper and π* and σ* orbitals of the substrate.
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