Communication: Double Bond Migration of a 1,5-Anhydro-3-C-p-Tolylsulfonyl-D-Hex-2-Enitol Derivative and the Corresponding 5a-Carba-Dl-Sulfonyl Sugar

Although the rate of proton abstraction (kinetic acidity) frequently plays an essential role in determination of reaction pathways and is of theoretical interest, 1 it is still controversial whether an oxygen atom activates or deactivates the abstraction of an α-hydrogen atom of an ether. For exampl...

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Published in:Journal of carbohydrate chemistry 2000-01, Vol.19 (6), p.783-788
Main Authors: Sakakibara, Tohru, Shindo, Miwa, Narumi, Shinya, Nagano, Chihiro, Kajihara, Yasuhiro
Format: Article
Language:English
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Summary:Although the rate of proton abstraction (kinetic acidity) frequently plays an essential role in determination of reaction pathways and is of theoretical interest, 1 it is still controversial whether an oxygen atom activates or deactivates the abstraction of an α-hydrogen atom of an ether. For example, it is well known that oxidative elimination of a seleno group gives an allyl ether as the major product, indicating the oxygen atom deactivates the kinetic acidity. 2 Abstraction of the equatorial hydrogen atom at C-2 of 6-methyl-1,3-oxathiane-3,3-dioxide 1 is slower than that at C-4. 3 On the other hand, the bridgehead hydrogen atom (H b ) adjacent to the oxygen atom of piperazinedione (2) is abstracted more readily than that of the alternative one (H a ). 4
ISSN:0732-8303
1532-2327
DOI:10.1080/07328300008544116