Catalysis of acyl transfer from amides to thiolate nucleophiles: The reaction of a distorted anilide with thioglycolic acid and ethyl 2-mercaptoacetate

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10829-10837

  Kellogg, B A ^a   Neverov, A A ^a   Aman, Ahmed M ^a   Brown, R S ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

THIOACID;

ARTICLE; DRUG SYNTHESIS; PH; REACTION ANALYSIS;

EID: 0029799203     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961312y     Document Type: Article

References (28)

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12. obs vs pH profile at high pH.
13. 4.
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17. nuc = 0.27 for rate-limiting attack of basic thiols. Since the attack on the protonated amide by thiolate is expected to be rate-limiting in our cases, a similar β should be expected.
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27. We thank a referee of an earlier version of this manuscript for this suggestion.
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