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ChemInform Abstract: Polar Cycloaddition of Monocyclic 1,2-Thiazinylium Salt and Transformation of the Cycloadducts to 1,2-Azathiabenzenes.

✍ Scribed by Hiroshi Shimizu; Takashi Hatano; Takayuki Matsuda; Tatsunori Iwamura

Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Polar Cycloaddition of Monocyclic 1,2-Thiazinylium Salt and Transformation of the Cycloadducts to 1,2-Azathiabenzenes.

-Diels-Alder reaction of the readily available thiazinylium perchlorate (VI) with the butadienes (VII) provides adducts across the C=S + bond. Deprotonation of the adducts yields 1,2-azathiabenzenes (IX) having sulfur at a bridgehead position. Interestingly, nucleophiles (XI) react with (VIIIa) to give the regiospecifically ring-opened products (XII). -(SHIMIZU, HIROSHI;

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