Stereochemistry of oxachlorocarbene SNi reactions

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1371-1374

  Moss, Robert A ^a   Fu, Xiaolin ^a   Tian, Jingzhi ^a   Sauers, Ronald ^a   Wipf, Peter ^b  

^a RUTGERS UNIVERSITY   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; CHLORIDE; HYDROCARBON; SOLVENT;

ARTICLE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 17444392139     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050185k     Document Type: Article

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34. See ref 18 in: Moss, R. A.; Ma, Y.; Sauers, R. R.; Madni, M. J. Org. Chem. 2004, 69, 3628. The repetition (Table 1) gave 57% retention.
35. 2O or HCl, respectively. In MeCN, 8-11% of trans-4-methyl-N-cyclohexylacetamide was formed by carbene attack on the solvent, followed by hydrolysis by traces of water.
36. - and carbene 10.
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38. We have made similar observations in the fragmentation of 7-norbornyloxychlorocarbene to 7-norbornyl chloride.
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