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By A.R. Katritzky, A.J. Boulton and J.M. Lagowski (Eds.)

ISBN-10: 0120206056

ISBN-13: 9780120206056

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9, 847 (1955). S. Sunner, Acta Chem. Scand. 17, 728 (1963). 155 S. Sunner, Acta Chem. Scand. 9, 837 (1955). 154s 156 W. K. Busfield, K. J. Ivin, H. Mackle, and P. A. G . Faraday Soc. 57, 1064 (1961). 157S. C. Abrahams, Quart. Rev. (London)10, 407 (1956). R. Katritzky and A. P. Ambler, in “Physical Methods in Heterocyclic Chemistry” (A. R. ), p. 161, Vol. 11. Academic Press, New York, 1963. 158 A. Sec. 1 ELECTRONIC STRUCTURE OF SULFUR COMPOUNDS 43 transitions ; satisfactory results were obtained only upon application of the method of limited configuration interaction.

LHMO characteristics'" of this compound suggest that it should be stable. It behaves as a base and is protonated in 0 . l N HCl. The authors suggest that the extra proton is attached to nitrogen (in accordance with the molecular diagram); for some puzzling evidence to the contrary see Section 111. 45P FIG. 12. 128Theoretically the synthesis of the parent cation (115) seems unpromising because an unoccupied bonding orbital is predictedZs (see also ref. 16). An interesting analogue of the benzotropylium cation, 2,3-thienotropylium cation, is mentioned in Section 111.

Garbuglio, M. Mammi, and G . Traverso, Gazz. Chim. Ital. 88, 104 106 1226 (1968). 111 S. Bezzi, M. Maxmni, and C. Garbuglio, Nature 182, 247 (1958). SeC. 1 ELECTRONIC STRUCTURE O F SULFUR COMPOUNDS 31 chemical study112proved that the compound in question has a bicyclic structure of an unusual type (see Section 11,E, thiothiophthene). d. 440 FIG. 9. le rr-electron density, and the high energy of the highest occupied 7 ~ molecular orbital (high oxidizability) in the few models of analogues of compound 8 examined theoretically" (97-101) indicate that all (97) (98) (99) (100) (101) these compounds will be quite unstable and difficult to prepare.

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Advances in Heterocyclic Chemistry, Vol. 5 by A.R. Katritzky, A.J. Boulton and J.M. Lagowski (Eds.)

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