Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
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Different Z/E-Selectivity Depending upon the Length of the Acyl Side Chain in the Formation of 2,2′-Diacyl-9,9′-bifluorenylidene
Atsushi OotaToshinobu ImaiAyumi YamazakiToru ObaMichinori KarikomiMasahiro Minabe
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2006 Volume 79 Issue 2 Pages 333-335

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Abstract

We studied the formation of 2,2′-diacyl-9,9′-bifluorenylidene from 2-acyl-9-bromofluorene via the corresponding intermediate 9-bromo-9,9′-bifluorenyl. It was found that dehydrobromination of the 9-bromo-9,9′-bifluorenyl derivatives occurred through the E2 elimination sequence, suggesting that the configuration of 9-bromo-9,9′-bifluorenyl isomers determined the stereochemistry of the product. Facile isomerization of the formed 9,9′-bifluorenylidenes may give the observed stereo-selectivity depending upon the length of the acyl side chain.

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© 2006 The Chemical Society of Japan
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