Single step stereospecific transformation of 2-phenylthio secondary amides into (Z)-3-chloro-2-phenylthio acrylamides

Anita R. Maguire; Maureen E. Murphy; Marcel Schaeffer; George Ferguson

doi:10.1016/0040-4039(94)02288-M

Single step stereospecific transformation of 2-phenylthio secondary amides into (Z)-3-chloro-2-phenylthio acrylamides

Anita R. Maguire
, Maureen E. Murphy
, Marcel Schaeffer
, George Ferguson

Research output: Contribution to journal › Article › peer-review

Abstract

α-Phenylthio secondary propanamides 1a-e are converted stereospecifically on treatment with NCS to the analogous (Z)-α-phenylthio-β-chloro propenamides 2a-e. Extension to longer chain secondary amide derivatives 1f-g is also possible, albeit less efficiently and without any appreciable stereoselectivity.

Original language	English
Pages (from-to)	467-470
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	3
DOIs	https://doi.org/10.1016/0040-4039(94)02288-M
Publication status	Published - 16 Jan 1995

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title = "Single step stereospecific transformation of 2-phenylthio secondary amides into (Z)-3-chloro-2-phenylthio acrylamides",

abstract = "α-Phenylthio secondary propanamides 1a-e are converted stereospecifically on treatment with NCS to the analogous (Z)-α-phenylthio-β-chloro propenamides 2a-e. Extension to longer chain secondary amide derivatives 1f-g is also possible, albeit less efficiently and without any appreciable stereoselectivity.",

author = "Maguire, \{Anita R.\} and Murphy, \{Maureen E.\} and Marcel Schaeffer and George Ferguson",

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AU - Maguire, Anita R.

AU - Murphy, Maureen E.

AU - Schaeffer, Marcel

AU - Ferguson, George

PY - 1995/1/16

Y1 - 1995/1/16

N2 - α-Phenylthio secondary propanamides 1a-e are converted stereospecifically on treatment with NCS to the analogous (Z)-α-phenylthio-β-chloro propenamides 2a-e. Extension to longer chain secondary amide derivatives 1f-g is also possible, albeit less efficiently and without any appreciable stereoselectivity.

AB - α-Phenylthio secondary propanamides 1a-e are converted stereospecifically on treatment with NCS to the analogous (Z)-α-phenylthio-β-chloro propenamides 2a-e. Extension to longer chain secondary amide derivatives 1f-g is also possible, albeit less efficiently and without any appreciable stereoselectivity.

UR - https://www.scopus.com/pages/publications/0028859721

U2 - 10.1016/0040-4039(94)02288-M

DO - 10.1016/0040-4039(94)02288-M

M3 - Article

AN - SCOPUS:0028859721

SN - 0040-4039

VL - 36

SP - 467

EP - 470

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -

Single step stereospecific transformation of 2-phenylthio secondary amides into (Z)-3-chloro-2-phenylthio acrylamides

Abstract

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