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Synthesis 2004(15): 2555-2559
DOI: 10.1055/s-2004-831199
DOI: 10.1055/s-2004-831199
PAPER
© Georg Thieme Verlag Stuttgart · New York
Lithiation of a Pyrrolo-Annulated Tetrathiafulvalene
Further Information
Received
3 June 2004
Publication Date:
26 August 2004 (online)
Publication History
Publication Date:
26 August 2004 (online)
Abstract
Mono- and bis-lithiations of N-tosyl monopyrrolotetrathiafulvalene provide novel methods for the introduction of substituents, such as alkyl and halogens, into the 4- and 6-positions of monopyrrolotetrathiafulvalenes.
Key words
carbanions - halogenation - organometallic - pyrrole - tetrathiafulvalene
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14Other lithium bases, such as n-BuLi and tert-BuLi were also tested. However, addition of n-BuLi or tert-BuLi to a solution of 3 caused detosylation producing the unprotected MPTTF derivative.13a
201H NMR spectroscopy revealed that the isolated product contained ca. 5% of 3.