Journal
ORGANIC LETTERS
Volume 15, Issue 9, Pages 2116-2119Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol400570r
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Funding
- EPSRC
- National Project FIRB - Futuro in Ricerca [RBFR083M5N]
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S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons.
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