Studies in the Cycloproparene Series. The Formation of Charge-Transfer Complexes from 1-Aryl- and 1-Diarylmethylidene-1H-cyclopropa[b]naphthalenes

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Contents Vol 58(2)

doi:10.1071/CH04233

Studies in the Cycloproparene Series. The Formation of Charge-Transfer Complexes from 1-Aryl- and 1-Diarylmethylidene-1H-cyclopropa[b]naphthalenes

Brian Halton ^A ^B, Jarrod M. Ward ^A

^A School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington, New Zealand.
^B Corresponding author. Email: brian.halton@vuw.ac.nz





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Australian Journal of Chemistry 58(2) 137–142 http://dx.doi.org/10.1071/CH04233
Submitted: 5 October 2004 Accepted: 17 December 2004 Published online: 21 February 2005

Abstract

The only charge-transfer (CT) complex formed from (p-dimethylaminophenyl)methylidene-1H-cyclopropa[b]naphthalene 7a is with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) 1 in acetonitrile. The methoxy-, thiomethyl-, and unsubstituted-phenyl analogues 7b–7d complex only with 2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-1,4-benzoquinodimethane (TCNQF₄) 2, and then only in dichloromethane; TCNQ 3, TCNE 4, and the o-CA 5 and p-CA 6 are without effect on any of 7a–7j. In contrast, the bis(dimethylaminophenyl)methylidene homologue 9a complexes with each of 1–5 but is the only diaryl derivative to do so. The polar parent, 1H-cyclopropa[b]naphthalene, does not form a CT complex with any of the acceptors employed.