Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides.

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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
  - ()
  - 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  - 
@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},
   = {()},
   = {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}
}
AUTHORSO'brien E, Murphy M, Lynch D, Schaeffer M, Kissane M, Chopra J, Ford A, Ferguson G, Maguire AR
YEAR2007
MONTHApril
JOURNAL_CODEOrganic and Biomolecular Chemistry
TITLEInvestigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides.
STATUSValidated
TIMES_CITED()
SEARCH_KEYWORD
VOLUME5
ISSUE8
START_PAGE1228
END_PAGE1241
ABSTRACTTreatment 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.
PUBLISHER_LOCATION
ISBN_ISSN
EDITION
URL
DOI_LINK10.1039/b618540a
FUNDING_BODY
GRANT_DETAILS