Categories: C-O Bond Formation >
Synthesis of thiocarbamates
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Recent Literature
Stable and readily available N,N'-di-Boc-substituted thiourea can be used
as a mild thioacylating agent when activated with trifluoroacetic acid anhydride.
Through thioacylation of nucleophiles, such as amines, alcohols, thiols, sodium
benzenethiolate, and sodium malonates, a series of thiocarbonyl compounds were
prepared with good chemical selectivity and functional group tolerance.
B.-L. Yin, Z.-G. Liu, J.-C. Zhang, Z.-R. Li, Synthesis, 2010,
991-999.
Electronically deactivated and/or sterically hindered substrates undergo the
Newman-Kwart rearrangement (NKR) at around 300°C using modern microwave
technology. In addition, several previously reported difficult examples were
re-investigated, and the NKR under the reported conditions was found to be a
reliable and high yielding reaction.
J. D. Moseley, P. Lenden, Tetrahedron, 2007,
63, 4120-4125.
Microwave technology has proven to be ideal for investigating the Newman-Kwart rearrangement (NKR)
at high
temperatures and facilitated the confirmation of many aspects of
this valuable reaction. Comparisons between thermal and microwave results
indicate no evidence of a significant microwave effect.
J. D. Moseley, R. F. Sankey, O. N. Tang, J. P. Gilday, Tetrahedron, 2006,
62, 4685-4689.
