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- W2950371056 abstract "4-Methyl-5-(substituted)imino-1,2,3,4-thiatriazolines 1 (R2 ≠ Me) undergo cycloaddition-elimination reactions with isocyanates to yield 4-methyl-5-(substituted)imino-1,2,4-thiadiazolidine-3-ones 5 via the thermodynamically less stable isomers 4. The latter have not been isolated, except for 4q which was shown to iso-merize rapidly into 5q with phenylsulfonyl isocyanate. The reactions of 1 are accelerated by using less bulky R2 substituents and more electrophilic isocyanates, in accordance with the viewpoint that 1 reacts as a masked 1,3-dipole. The products 4i-n (= 5i-n), derived from 1b, add isocyanates reversibly to give 2,3,4,5-tetrahydro-6aλ4-thia-1,3,4,6-tetraazapentalene-2,5-diones 9i-n, which have been isolated and characterized spectroscopically. Such compounds with a hypervalent sulfur atom thus occur as intermediates during the isomerization of 4 to 5 under the influence of isocyanates." @default.
- W2950371056 created "2019-06-27" @default.
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- W2950371056 date "1991-02-01" @default.
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- W2950371056 title "Cycloaddition-elimination reactions of 4-methyl-5-(substituted)-imino-Δ<sup>2</sup>-1,2,3,4-thiatriazolines with isocyanates" @default.
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- W2950371056 doi "https://doi.org/10.1002/jhet.5570280238" @default.
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