Abstract:. 58,2784 (1980). The reactions of ethyl(trichloromethyl)carbinol, dimethyl(trichloromethyl)carbinol, (trichloromethyl)vinylcarbinol, ethynyl (trichloromethyl)carbinol, and 1,1,1,-trichloro-3-nonyn-2-01 have been studied with the following reagents. Methanolicpotassium hydroxide: a-methoxy acids are formed in 70 and 79% yields with the ethyl-and vinylcarbinols respectively. Double bond migration to the conjugated position was observed with the vinylcarbinol. Thiourea: substituted 2-imino-4-thiazolidinones are … Show more
“…They also reported the first preparation of asymmetric trichloromethyl carbinols using an enantioselective oxazaborolidine-based reduction of the corresponding trichloromethyl ketones . Although these investigators have made notable contributions toward the application of trichloromethyl carbinols in Jocic-type reactions, examinations into the reactivity of alkenyl trichloromethyl carbinols in such reactions are conspicuously lacking …”
The reaction of alkenyl trichloromethyl carbinols with various nucleophiles under protic basic conditions reveals that mercaptans participate by alpha-substitution (S(N)2) of the intermediate alkenyl gem-dichloroepoxides. Conversely, hydroxide results in preferential gamma-substitution with stereoselective allylic transposition (S(N)2'). Regioselectivity with alkoxides depends upon the level of alkene substitution. [reaction: see text]
“…They also reported the first preparation of asymmetric trichloromethyl carbinols using an enantioselective oxazaborolidine-based reduction of the corresponding trichloromethyl ketones . Although these investigators have made notable contributions toward the application of trichloromethyl carbinols in Jocic-type reactions, examinations into the reactivity of alkenyl trichloromethyl carbinols in such reactions are conspicuously lacking …”
The reaction of alkenyl trichloromethyl carbinols with various nucleophiles under protic basic conditions reveals that mercaptans participate by alpha-substitution (S(N)2) of the intermediate alkenyl gem-dichloroepoxides. Conversely, hydroxide results in preferential gamma-substitution with stereoselective allylic transposition (S(N)2'). Regioselectivity with alkoxides depends upon the level of alkene substitution. [reaction: see text]
Untersucht wird die Reaktion von Trichlormethylcarbinolen (II), (VII) und (XIV) mit Nucleophilen in alkalischem Milieu, die im l. Schritt über 3‐substituierte 2,2‐Dichlor‐epoxide verläuft.
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