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Molbank 2017, 2017(1), M930; doi:10.3390/M930

2-(tert-Butyl)-4-phenyloxetane

Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari “A. Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, Italy
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Authors to whom correspondence should be addressed.
Academic Editor: Norbert Haider
Received: 22 December 2016 / Revised: 24 January 2017 / Accepted: 7 February 2017 / Published: 10 February 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

The two geometric isomers of 2-(tert-butyl)-4-phenyloxetane have, for the first time, been prepared starting from the commercially available 4,4-dimethyl-1-phenylpentane-1,3-dione. The latter was reduced with NaBH4 to give a mixture of diastereomeric syn and anti diols which were then stereospecifically cyclized into the corresponding oxetanes with an overall yield for the two steps of 69.6%. The newly synthesized stereoisomeric four-membered oxygenated heterocycles were separated by column chromatography on silica gel and fully spectroscopically characterized. View Full-Text
Keywords: oxetanes; diols; diastereoisomers; cyclization reactions; NMR; heterocycles oxetanes; diols; diastereoisomers; cyclization reactions; NMR; heterocycles
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Perna, F.M.; Vitale, P.; Summa, S.; Capriati, V. 2-(tert-Butyl)-4-phenyloxetane. Molbank 2017, 2017, M930.

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