Synthesis of α-Halocinnamate Esters via Solvolytic Rearrangement of Trichloroallyl Alcohols
Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-α-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement.Micharl addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides.The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.
Kruper, William J.,Emmons, Albert H.
p. 3323 - 3329
(2007/10/02)
HOMOLYTIC ADDITION OF ALIPHATIC ALCOHOLS TO TETRACHLOROETHYLENE IN THE LIQUID PHASE
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Salamandra, L. K.,Vol'kenshtein, Yu. B.,Bogdanov, V. S.,Botnikov, M. Ya.,Kadentsev, V. I.,Nikishin, G. I.
p. 1401 - 1405
(2007/10/02)
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