Synthesis of an Optically Active Triorganostannyl Ketone

Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
· DOI :10.1002/bscb.19770860107
Marcel Gielen38
Estimated H-index: 38
(Vrije Universiteit Brussel),
Stéphane Simon8
Estimated H-index: 8
(ULB: Université libre de Bruxelles)
Racemic p-(cyclohexylmethyl-l-naphthylstannyl) acetophenone (I) is transformed into its menthydrazone which is, after four recrystallizations, reconverted to optically active (I), [α]20°436 +0.25° ± 0.05°. Several methods have been used to determine the optical purity of optically active (I) without success.
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Many organotin compounds are optically stable for long periods so that all the reactions transforming one of them into another can be studied from the stereochemical point of view. Several stereoselective reactions at tin have already been found. However the stereochemistries and even the stereoselectivities have not yet been determined (if the H—D exchange is not taken into account) because the optical purities (and a fortiori the absolute configurations) of the starting materials and of the re...
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