Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: Evidence for the loss of stereoselectivity at the limits of diffusion control

Journal of the American Chemical Society

Volumn 128, Issue 26, 2006, Pages 8671-8677

  Shenoy, Siddhartha R ^a   Smith, Deborah M ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIFFUSION; RATE CONSTANTS; SUBSTITUTION REACTIONS;

CYCLIC OXOCARBENIUM; DIASTEREOSELECTIVITY; STEREOELECTRONIC MODELS;

CYANIDES;

CARBENOID; CYANIDE; ION; OXOCARBENIUM ION; TRIMETHYLSILYL CYANIDE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; DIFFUSION; ELECTRON TRANSPORT; MODEL; STEREOCHEMISTRY; STEREOELECTRONIC MODEL; SUBSTITUTION REACTION;

ACETALS; CYANIDES; DIFFUSION; IONS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; ORGANOSILICON COMPOUNDS; STEREOISOMERISM; TRIMETHYLSILYL COMPOUNDS;

EID: 33745714287     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061110u     Document Type: Article

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