Trimethylsilylcyanation of aldehydes and ketones catalyzed by diorganotin dichlorides

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2525-2528

  Whitesell, James K ^a   Apodaca, Richard ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; ORGANOSILICON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029983320     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00386-3     Document Type: Article

References (35)

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24. Reactions with aldehydes were generally mildly exothermic. Initial cooling was employed to prevent significant temperature increase.
25. General experimental procedure: Trimethylsilyl cyanide (CAUTION: Toxic!, 3.20 mmol, 1.3 eq) was added to the untreated organotin catalyst at room temperature under nitrogen. The homogeneous mixture was frozen in an ice bath after which the untreated aldehyde or ketone (2.46 mmol, 1 eq) was added and the ice bath was removed. After the indicated time, the resulting oil was pipetted onto a short plug of Florisil® and eluted with Skelly B. The catalyst-free product was obtained by evaporation of the solvent at water aspirator pressure.
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