Annelation reactions of 3-phenylthiobut-3-en-2-one. A new method of constructing fused phenols

…, M Okada, M Yamada, K Negoro

Index: Takaki, Ken; Okada, Michikazu; Yamada, Michio; Negoro, Kenji Journal of the Chemical Society, Chemical Communications, 1980 , # 24 p. 1183 - 1184

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Abstract

Reactions of 3-phenylthiobut-3-en-2-one with enolate anions of cyclohexanone and cyclopentanone gave good yields of 8a-hydroxy-3-phenylthio-2-decalone and 3a-hydroxy-6- phenylthiohexahydroindan-5-one which were readily converted into 5, 6, 7, 8-tetrahydro-2- naphthol and indan-5-ol, respectively, on exposure to toluene-p-sulphonic acid: a similar reaction of the enolate of cycloheptanone and subsequent treatment with sodium ethoxide ...