IRIS publication 5956752
Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides.
RIS format for Endnote and similar
TY - JOUR - O'brien E, Murphy M, Lynch D, Schaeffer M, Kissane M, Chopra J, Ford A, Ferguson G, Maguire AR - 2007 - April - Organic and Biomolecular Chemistry - Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides. - Validated - Altmetric: 1 () - 5 - 8 - 1228 - 1241 - Treatment of a series of alpha-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous alpha-thio-beta-chloroacrylamides. The mechanistic pathway has been established through isolation and characterisation of intermediate compounds. The scope of the transformation has been explored-aryl and alkylthio substituents, primary, secondary and tertiary amides can be employed. In most instances, the chloroacrylamides are formed exclusively as the Z-stereoisomer; however, with tertiary propanamides or with amides derived from butanoic or pentanoic acid a mixture of E- and Z-stereoisomers is formed. - 10.1039/b618540a DA - 2007/04 ER -
BIBTeX format for JabRef and similar
@article{V5956752, = {O'brien E, Murphy M and Lynch D, Schaeffer M and Kissane M, Chopra J and Ford A, Ferguson G and Maguire AR }, = {2007}, = {April}, = {Organic and Biomolecular Chemistry}, = {Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides.}, = {Validated}, = {Altmetric: 1 ()}, = {5}, = {8}, pages = {1228--1241}, = {{Treatment of a series of alpha-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous alpha-thio-beta-chloroacrylamides. The mechanistic pathway has been established through isolation and characterisation of intermediate compounds. The scope of the transformation has been explored-aryl and alkylthio substituents, primary, secondary and tertiary amides can be employed. In most instances, the chloroacrylamides are formed exclusively as the Z-stereoisomer; however, with tertiary propanamides or with amides derived from butanoic or pentanoic acid a mixture of E- and Z-stereoisomers is formed.}}, = {10.1039/b618540a}, source = {IRIS} }
Data as stored in IRIS
AUTHORS | O'brien E, Murphy M, Lynch D, Schaeffer M, Kissane M, Chopra J, Ford A, Ferguson G, Maguire AR | ||
YEAR | 2007 | ||
MONTH | April | ||
JOURNAL_CODE | Organic and Biomolecular Chemistry | ||
TITLE | Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides. | ||
STATUS | Validated | ||
TIMES_CITED | Altmetric: 1 () | ||
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VOLUME | 5 | ||
ISSUE | 8 | ||
START_PAGE | 1228 | ||
END_PAGE | 1241 | ||
ABSTRACT | Treatment of a series of alpha-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous alpha-thio-beta-chloroacrylamides. The mechanistic pathway has been established through isolation and characterisation of intermediate compounds. The scope of the transformation has been explored-aryl and alkylthio substituents, primary, secondary and tertiary amides can be employed. In most instances, the chloroacrylamides are formed exclusively as the Z-stereoisomer; however, with tertiary propanamides or with amides derived from butanoic or pentanoic acid a mixture of E- and Z-stereoisomers is formed. | ||
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DOI_LINK | 10.1039/b618540a | ||
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