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Rearrangement of 1-aryl-2,2-Dichloro-1-Alkanones and 1-Aryl-2,2-Dichloro-1-Alkanols with Methylmagnesium Iodide

✍ Scribed by Norbert de Kimpe; Roland Verhé; Laurent de Buyck; N. Schamp

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
734 KB
Volume
88
Category
Article
ISSN
0037-9646

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✦ Synopsis

sium iodide in ether under reflux into highly sterically hindered alkohols. The mechanism proceeds by a pseudo pinacol type rearrangement of the initially formed carbonyl adduct. The mechanism of the rearrangement was proven by the synthesis of authentic reaction intermediates. The rearrangement was also extended to l-aryl-2,2-dichloro-l-alkanols which behaved analogously towards methylmagnesium iodide.

l-Aryl-2,2-dichloro-l-alkanones were shown to rearrange with methyl magne-

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## C1 c 1 (3) were formed together with (1). The NMR parameters of (l), its cis and trans isomers and (2) were obtained in C,D, solution at 100 MHz. Theoretical spectra of (1) at 60 MHz were simulated with the aid of a computer, using as input the NMR parameters obtained at 100 MHz and good agree