Regio- and stereo-chemical control in the nickel-catalysed addition of HCN to alkynes. A simple synthesis of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles

Gary D. Fallon, Neil J. Fitzmaurice, W. Roy Jackson, Patrick Perlmutter

Research output: Contribution to journalArticleResearchpeer-review

16 Citations (Scopus)

Abstract

By varying the steric bulk of silicon substituents attached to alk-1-ynes it is possible to control, to a high degree, the regiochemical outcome of nickel(0)-catalysed hydrocyanations of alk-1-ynes: the crystal structure of one adduct is included which establishes that the stereochemical outcome of the reaction is a result of addition of HCN to the alkyne to give an (E)-product; overall, these results constitute a simple method for the preparation of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles.

Original languageEnglish
Pages (from-to)4-5
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number1
DOIs
Publication statusPublished - 1 Jan 1985

Cite this

@article{d1d3f2b0b27b4ee48d6742d1bea089c3,
title = "Regio- and stereo-chemical control in the nickel-catalysed addition of HCN to alkynes. A simple synthesis of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles",
abstract = "By varying the steric bulk of silicon substituents attached to alk-1-ynes it is possible to control, to a high degree, the regiochemical outcome of nickel(0)-catalysed hydrocyanations of alk-1-ynes: the crystal structure of one adduct is included which establishes that the stereochemical outcome of the reaction is a result of addition of HCN to the alkyne to give an (E)-product; overall, these results constitute a simple method for the preparation of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles.",
author = "Fallon, {Gary D.} and Fitzmaurice, {Neil J.} and Jackson, {W. Roy} and Patrick Perlmutter",
year = "1985",
month = "1",
day = "1",
doi = "10.1039/c39850000004",
language = "English",
pages = "4--5",
journal = "Journal of the Chemical Society - Series Chemical Communications",
issn = "0022-4936",
publisher = "The Royal Society of Chemistry",
number = "1",

}

Regio- and stereo-chemical control in the nickel-catalysed addition of HCN to alkynes. A simple synthesis of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles. / Fallon, Gary D.; Fitzmaurice, Neil J.; Jackson, W. Roy; Perlmutter, Patrick.

In: Journal of the Chemical Society, Chemical Communications, No. 1, 01.01.1985, p. 4-5.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Regio- and stereo-chemical control in the nickel-catalysed addition of HCN to alkynes. A simple synthesis of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles

AU - Fallon, Gary D.

AU - Fitzmaurice, Neil J.

AU - Jackson, W. Roy

AU - Perlmutter, Patrick

PY - 1985/1/1

Y1 - 1985/1/1

N2 - By varying the steric bulk of silicon substituents attached to alk-1-ynes it is possible to control, to a high degree, the regiochemical outcome of nickel(0)-catalysed hydrocyanations of alk-1-ynes: the crystal structure of one adduct is included which establishes that the stereochemical outcome of the reaction is a result of addition of HCN to the alkyne to give an (E)-product; overall, these results constitute a simple method for the preparation of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles.

AB - By varying the steric bulk of silicon substituents attached to alk-1-ynes it is possible to control, to a high degree, the regiochemical outcome of nickel(0)-catalysed hydrocyanations of alk-1-ynes: the crystal structure of one adduct is included which establishes that the stereochemical outcome of the reaction is a result of addition of HCN to the alkyne to give an (E)-product; overall, these results constitute a simple method for the preparation of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles.

UR - http://www.scopus.com/inward/record.url?scp=33644577067&partnerID=8YFLogxK

U2 - 10.1039/c39850000004

DO - 10.1039/c39850000004

M3 - Article

SP - 4

EP - 5

JO - Journal of the Chemical Society - Series Chemical Communications

JF - Journal of the Chemical Society - Series Chemical Communications

SN - 0022-4936

IS - 1

ER -