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2372 (1928). Vorozhcov and V. Ya. Rodionov, Dokl. Akad. Nauk SSSR 134, 1085 129 130 (1960). Wynberg and A. Bantjes, J . Am. Chena. 82, 1447 (1960). 38 R. ZAHRADN~K [Sec. 11. E. molecular diagrams16of the analogues 120 and 121 of sesquifulvalene (18) are more encouraging, however. E. ANALOGUES OF HYDROCARBONS DERIVED BY SUBSTITUTING SULFUR FOR A TERTIARY CARBONATOM These compounds, at present hypothetical, contain a a-tervalent sulfur atom. Theoretical studies were performedla for models of compounds 122-126; the first two are, in a sense, analogues of bicyclic compounds.

11. 1. Figure 12 presents the molecular diagram of an interesting benzo ~ ~ energy derivative of a sulfur-aza analogue of h e ~ t a 1 e n e . 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.

50 Sec. 11. 1 ELECTRONIC STRUCTURE OF SULFUR COMPOUNDS 19 accounted for by the values of localization energies while r-electron densities lead to incorrect predictions. 57, 58 Formal substitution of two benzene double bonds by sulfur atoms leads to the four-membered heterocycle 1,a-dithiete (37). This compound has not been synthesized, although derivative 38 is k n ~ w n , ~6og * and dicyano-l,2-dithiete (39) is very probably an intermediate in some reactions of thiacyanocarbons (see below). Models of both combut pounds have been studied t h e ~ r e t i c a l l y ,6~1 ~ .

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