13713-79-6Relevant articles and documents
Reactions of epoxides-XXIV. The BF3-catalysed rearrangement of 4,5- and 5,6-epoxycholestanes
Blackett,Coxon,Hartshorn,Richards
, p. 4999 - 5005 (1969)
4α,5α, 4β,5β- and 5β, 6β-Epoxycholestanes give backbone rearranged compounds on BF3-catalysed rearrangement. Solvent changes markedly affect the products of rearrangement. 4α-Hydroxycompounds arise from the 4β,5β-epoxide on BF3-catal
Allinger et al.
, p. 3626,3628 (1961)
Reactions of epoxides. XVII. "Backbone rearrangements" of cholest-5-ene and 5,6alpha-epoxy-5alpha-cholestane.
Blunt,Hartshorn,Kirk
, p. 149 - 153 (1969)
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Reactions of steroidal 5,6-epoxides and cyclohexene oxide with aluminum alkoxides
Holland, Herbert L.,Khan, Saeed R.
, p. 2763 - 2768 (2007/10/02)
The isomeric 5,6α- and 5,6β-epoxycholestanes, in addition to an analogous series of compounds substituted at C-3 with hydroxy (α or β stereochemistry) or ethylene ketal groups, have been treated with aluminum isopropoxide or tert-butoxide.The latter series of reactions did not give identifiable material, but aluminum isopropoxide gave products derived from epoxide opening and rearrangement in all cases.With epoxides unsubstituted at C-3, aluminum isopropoxide functioned as a Lewis acid in promoting epoxide rearrangements.In the presence of a C-3 alcohol function, additional products were obtained arising from fragmentation of the C-4,C-5 bond, or from β-elimination of the epoxide involving the loss of a C-7 hydrogen.Meerwein-Pondorff reduction of product carbonyl groups was also observed.C-3 ketal substituted epoxides were rearranged cleanly to 6-hydroxy-Δ4-3-ketones.Cyclohexene oxide reacted with aluminum isopropoxide (but not with tert-butoxide) to give two products arising from epoxide addition reactions.Structures for these products are proposed based on their 13C nmr spectra, and a possible route for their formation is presented.None of the epoxides examined in this study reacted with magnesium methoxide.
Reactions with Phosphororganic Compounds XLVIII. On the Behaviour of cis-1,2-Diols towards TPP/DEAD
Penz, Gottfried,Zbiral, Erich
, p. 1045 - 1054 (2007/10/02)
Reaction of the vicinal diols of steroids 1, 5, 7, 10, 13, and 16 with TPP/DEAD yields both regio- and stereospecifically the oxosteroids 2, 6, 8, 11, 14, and 15 by displacement of an axial hydrogen and extrusion of TPPO besides the cholest-4-en-6-ols 9 a