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Issue 11, 2018
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NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes

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Abstract

(2,3-Dihydrobenzo[b][1,4]oxathiin-3-yl)methanols were synthesized via reactions of aryloxymethylthiiranes and N-bromosuccinimide (NBS) in DMSO under microwave irradiation. The reaction mechanism was proposed as an intramolecular aromatic electrophilic substitution of 1-bromo-2-(aryloxymethyl)thiiran-1-iums, generated from aryloxymethylthiiranes and NBS, and the subsequent DMSO nucleophilic ring opening reaction of thiiran-1-iums followed by the water displacement. The current method provides a direct and simple strategy in the efficient preparation of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from readily available aryloxymethylthiiranes.

Graphical abstract: NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes

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Publication details

The article was received on 07 Mar 2018, accepted on 11 Apr 2018 and first published on 13 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ01117F
Citation: New J. Chem., 2018,42, 9037-9044
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    NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes

    J. Dong and J. Xu, New J. Chem., 2018, 42, 9037
    DOI: 10.1039/C8NJ01117F

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