Issue 2, 1980
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Stereospecific reduction of 3-hydroxy-3H-indoles and of their corresponding N-oxides with NaBH4 and LiAIH4. Synthesis of true 1-hydroxy-2,3-disubstituted indoles. Crystal and molecular structure of 3-hydroxy-2,3-diphenylindoline

Corrado Berti,   Lucedio Greci,   Marino Poloni,   Giovanni Dario Andreetti,   Gabriele Bocelli  and  Paolo Sgarabotto  

Abstract

3-Hydroxy-3H-indoles (1) and their corresponding N-oxides (5) undergo stereospecific reduction at the double C[double bond, length half m-dash]N bond giving the indoline derivatives (2) and (6) respectively, which, in acidic medium, lose water to give the 2,3-disubstituted indoles (3) and (7) whose physical and spectroscopic data are not in agreement with those reported previously. The structure of 3-hydroxy-2,3-diphenylindoline, one of the reduction products, was determined by X-ray diffraction, and it was shown that hydrogen adds at C-2 cis to the hydroxy-group on C-3. 3,3-Disubstituted-3H-indoles with two organic radicals on C-3 give a mixture of stereoisomers.

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Article information

DOI
https://doi.org/10.1039/P29800000339
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1980, 339-346

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Stereospecific reduction of 3-hydroxy-3H-indoles and of their corresponding N-oxides with NaBH4 and LiAIH4. Synthesis of true 1-hydroxy-2,3-disubstituted indoles. Crystal and molecular structure of 3-hydroxy-2,3-diphenylindoline

C. Berti, L. Greci, M. Poloni, G. D. Andreetti, G. Bocelli and P. Sgarabotto, J. Chem. Soc., Perkin Trans. 2, 1980, 339 DOI: 10.1039/P29800000339

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