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Reactions between lithiated 1,3-dithiane oxides and trialkylboranes

Saleh, Basil A., Smith, Keith, Elliott, Mark C. and El-Hiti, Gamal A. 2021. Reactions between lithiated 1,3-dithiane oxides and trialkylboranes. Journal of Sulfur Chemistry 42 (6) , pp. 591-603. 10.1080/17415993.2021.1971670

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Various 2-substituted-1,3-dithiane oxides (1-oxide and 1,3-dioxide) have been metalated and reacted for the first time with a trialkylborane (trioctylborane). The 2-chloro-1,3-dioxide results in migration of an octyl group from boron to carbon with the displacement of chloride and gives nonanoic acid after oxidation, but there is no evidence for a second migration involving displacement of a sulfenate group. The reaction involving lithiation of the 2-methoxy-1-oxide results in two migrations, with the displacement of both the methoxy group and the thiolate unit of the dithiane ring, giving dioctyl ketone after oxidation, but the yield is low, primarily because thiophilic addition of the lithiating agent predominates over lithiation. Again, there is no evidence for the displacement of the sulfenate unit. However, the intermediate prior to oxidation can be treated with trifluoroacetic anhydride to induce a Pummerer rearrangement, and the presumed trifluoroacetoxyalkylthiolate group then acts as a novel leaving group and is displaced, resulting in trioctylmethanol on oxidation, but the yield is again very low.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Additional Information: This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial-NoDerivatives License (, which permits non-commercial re-use, distribution, and reproduction in any medium, provided the original work is properly cited, and is not altered, transformed, or built upon in any way.
Publisher: Taylor & Francis
ISSN: 1741-5993
Funders: Cardiff University; University of Basrah; King Saud University [grant number RSP-2021/404
Date of First Compliant Deposit: 28 September 2021
Date of Acceptance: 18 August 2021
Last Modified: 10 Nov 2021 11:54

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