Journal of Organic Chemistry p. 3855 - 3861 (1982)
Update date:2022-08-05
Topics:
Beak, Peter
Becker, Peter D.
The formation of 5 and 17, synthetic equivalents of the α-lithioalkylthio and α-lithiodialkylthio functions, respectively, by deprotonations of the corresponding carbamate 4 and thioester 16 are reported.The reactions of these formally dipole-stabilized carbanions with a variety of electrophiles and their use in synthese of 2,3-substituted thiiranes are demonstrated.The rearrangement of 17 to an α-thiol ketone is shown to be intramolecular by a double labeling experiment.Potentially chiral or conformationally isomeric α'-lithio thioesters are found to be racemized and equilibrated.Formations of secondary α'-lithio thioesters in medium chain, β'-dimethylamino, and allyl systems are reported while β'-alkoxy groups are shown to eliminate to give vinyl thio esters which undergo further metalation.The kinetic acidity of a methyl thioester is shown to be comparable to a propenyl thioester and greater then an ethyl thioester.
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Doi:10.1021/om049284c
(2005)Doi:10.1002/ardp.19833160211
(1983)Doi:10.1039/jr9370001619
(1937)Doi:10.1039/jr9490000439
(1949)Doi:10.1002/hlca.19430260212
(1943)Doi:10.1016/S0040-4039(00)81564-6
(1983)