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A high temperature investigation using microwave synthesis for electronically and sterically disfavoured substrates of the Newman-Kwart rearrangement

Jonathan D. Moseley* and Philip Lenden

*AstraZeneca, Process Research and Development, Avlon Works, Severn Road, Hallen, Bristol BS10 7ZE, UK, Email: jonathan.moseleyastrazeneca.com

J. D. Moseley, P. Lenden, Tetrahedron, 2007, 63, 4120-4125.

DOI: 10.1016/j.tet.2007.02.101


Abstract

Electronically deactivated and/or sterically hindered substrates undergo the Newman-Kwart rearrangement (NKR) at around 300C 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.

see article for more examples



The Newman-Kwart rearrangement re-evaluated by microwave synthesis

J. D. Moseley, R. F. Sankey, O. N. Tang, J. P. Gilday, Tetrahedron, 2006, 62, 4685-4689.


Key Words

Newman-Kwart Rearrangement, Microwave Synthesis, Thiocarbamates


ID: J72-Y2007-4210