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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


Book ID
111714459
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
226 KB
Volume
40
Category
Article
ISSN
0040-4039

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ChemInform Abstract: Polar Cycloaddition
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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

Novel polar cycloaddition of 1,2-thiazin
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Dibenzo[e,e][1, 2] thiazinylium tetrafluoroborate underwent polar cycloaddition with several 1,3-butadienes to afford new sulfur-nitrogen-containing s~lfonium heterocycles in good yields: The cycloaddition with unsymmetrical 1,3-butadiene, isoprene afforded two regToisomeric adducts. Deprotonatio

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Novel Polar Cycloaddition of 1,2-Thiazinylium Salt. -Treatment of the thiazine 5-oxide (I) according to A) affords a thiazinylium tetrafluoroborate which undergoes cycloaddition with the butadienes (II) and (V) to give heterocyclic adducts. Ring transformation of cycloadduct (IIIa) yields the pyrrol