Solvolysis, Substitution, Elimination, and Reduction

Solvolysis, Substitution, Elimination, and Reduction.—Studies on the solvolysis of 3p-tosyloxy-5,10-secocholest-1 (10)-en-5-ones have been reported5 and are complementary to those reported earlier6 on similar compounds. Considerable double bond participation was observed for the Z-3a-compound (1), the i 3a-compound (2), 

6 See Terpenoids and Steroids , ed. J. R. Hanson (Specialist Periodical Reports) The Royal Society of Chemistry, London, 1982, Vol. 11, p. 187. 

Calculations suggested that the preferred elimination of 3-substituted andro-stanes to give A2- rather than A3-compounds could not be explained alone by differences in calculated heats of formation. Differences in the energies of the respective transition states appeared to be important.15 Dehydration of the cyclobutanol (5) gave largely the exo-alkene (7) but the tetradeuterio-compound (6) 

Fuhrer, L. Lorenc, V. Pavlovic, G. Rihs, G. Rist, J. Kalvoda, and M. Lj. Mihailovid, Helv. Chim. Acta, 1981, 64, 703. 

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