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

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

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L. two hybrid 3pd2 orbitals belonging to the sulfur atom take part in the conjugation. Thiophene,14, 31-39 benzo[b]thiophene,34 benzo[c]40 have been studied in terms of t h i ~ p h e n eand , ~ ~diben~othiophene~~. this model. A satisfactory interpretation of the course of electrophilic substitution reactions of these molecules can be obtained from T electron densities based on Model B or a modified Model A (A3). With benzo derivatives of thiophene, the original version of Model A fails to account satisfactorily for the reactivity data.

11. 1 ELECTRONIC STRUCTURE OF SULFUR COMPOUNDS 17 hydride adds readily a t these positions. Recently, the course of radical phenylation of dibenzothiophene (29) was examined thoroughly46 and the following reactivity order found : 1 4 > 3 > 2. The sterically less favorable positions 1 and 4 are much more reactive than the others, which is in good agreement4"with the values of the free valence reported in previous studies of dibenzothiophene. 4 3 However, the correct reactivity order for positions 2 and 3 has onlyrecently been obtained.

SOC. 83, 3434 (1961). 60 C. G. Krespan, B. C. McKusick, and T. L. Cairns, J . Am. C h . Soc. 82,1515 57 58 (1960). 61 H. E. Simmons, D. C. Blometrom, and R. D. Vest, J . Am. Soc. 84, 6a H. E. Simmons, D. C. 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.

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