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By A.R. Katritzky, A.J. Boulton and J.M. Lagowski (Eds.)
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 5
Z h a d n i k , unpublished results (1963). 24 R. E. Davis, J . Org. Chem. 23, 216 (1958). 22 Sec. 11. 1 ELECTRONIC STRUCTURE OF SULFUR COMPOUNDS 15 istry of this compound and its derivatives has been thoroughly reviewed. 25-28 Numerous benzo derivatives of thiophene (27-36) have been synthesized and studied theoretically. 5 The first quantum chemical study of thiophene was due to Wheland and P a ~ l i n who g ~ ~used a model neglecting d-orbital participation and demonstrated that the inductive effect must be allowed for in order to explain its chemical reactivity.
Blornstrom, and R. D. Vest, J . Am. Chem. Soc. 84, 63 H. E. Simmons, D. C. Blomstrom, and R. D. Vest, J . Am. Chem. 84, 4782 (1962). 4756 (1962). 4772 (1962). H. E. Simmons,R. D. Vest, D. C. Blometrom,J. R. Roland, and T. L. C~irns, J . Am. Chem. Soc. 84,4746 (1962). 65 G. BEhr, Angew. Chem. 68,526 (1956). 66 G. BEhr and G. Schleitzer, Chem. Ber. 88, 1771 (1955). 67 G. Biihr and G . Schleitzer, Chem. Ber. 90, 438 (1957). 64 20 [Sec. 11. l. R. ZAHRADN~K Models of compounds 40,41, and 43 have been studied theoreticallyZS assuming complete planarity.
D. Analogues of Cyclodecapentaene (4). The prospect of synthesizing these compounds is not particularly encouraging for the reasons stated in the section dealing with analogues of the cyclononatetraenide anion; the HMO treatmentla makes it seem probable nevertheless that a compound like 58hould be prepared. Compounds 59 and 60, on the other hand, probably can not. 2 . Parent Skeleton: A Non-Alternant Hydrocarbon a. The five-membered ring system is the smallest odd-membered ring from which a sulfur compound may be derived (at least formally, by Model A).
Advances in Heterocyclic Chemistry, Vol. 5 by A.R. Katritzky, A.J. Boulton and J.M. Lagowski (Eds.)