Polyfluoroaryl organometallic compounds. Part XV. Synthesis and rearrangement of polyhalogenoaryl α-diketones
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2464-2469
- https://doi.org/10.1039/p19720002464
Abstract
Decafluoro- and decachloro-benzil have been obtained by reactions of the corresponding aryl-lithiums with dimethyl oxalate in a process shown to involve the intermediacy of adducts. The unsymmetrical benzils C6F5·CO·-CO·C6H5 and C6H5·CO·CO·C6Cl5 have been obtained by sequential additions of different aryl-lithiums to dimethyl or diethyl oxalate. Decafluorobenzil undergoes fast base-catalysed rearrangement to the benzilic acid or ester and it is proposed that the transition-state in the process has considerable benzenide character. Attempts to synthesise perfluorophenanthrene-9,10-quinone. by an analogous route, led only to products of rearrangement.Keywords
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