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Paper | Regular issue | Vol 36, No. 2, 1993, pp.281-286
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6144
Reactivity of Ethanediyl S,S-Acetals -- 5. On the Aromatization of the Ring A in 3-Oxosteroid Derivatives

Romualdo Caputo, Carla Ferreri, Giovanni Palumbo,* Silvana Pedatella, and Francesco Russo

*Dipartimento di Chimica Organica e Biologica, Università di Napoli "Federico II", Via Mezzocannone 16, I-80134 Napoli, Italy

Abstract

Ethanediyl S,S-acetal (1,3-dithiolane) derivatives of 3-oxosteroids, when treated with bromine in anhydrous chloroform at room temperature, undergo ring A aromatization following a dienone-benzene like steroidal skeleton rearrangement that leads to 1,4-dithian fused 4-methylestranes. The easy replacement of the sulphur atoms may afford 4-methylestranes with variously substituted A rings.