On alkylideneamidosulfenyl chlorides and 1-Thia-2-azoniaallene salts

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2002
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Wirschun, Wolfgang G.
Hitzler, Martin G.
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Helvetica chimica acta. 2002, 85(9), pp. 2627-2635. ISSN 0018-019X. eISSN 1522-2675. Available under: doi: 10.1002/1522-2675(200209)85:9<2627::AID-HLCA2627>3.0.CO;2-H
Zusammenfassung

X-Ray-diffraction analysis of tBu2CNSCl (4b) revealed an almost linear CNS unit with an SN bond order of ca. 1.9 (Fig. 1), in agreement with the structure of a 1-thia-2-azoniaallene chloride. With SCl2 and SbCl5, compound 4b was transformed into the imidosulfurous dichloride 6 (Scheme 2). With morpholine, compounds 4b and 6 afforded the sulfenamide 7and the aminosulfonium salt 8, respectively. The (diarylmethylene)amidosulfenyl chlorides 4g,h,i reacted with SbCl5 to give SbCl salts of the 1,2-benzisothiazoles 9a,b,d, most likely via 1-thia-2-azoniaallene intermediates 2 (Scheme 3).

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ISO 690WIRSCHUN, Wolfgang G., Martin G. HITZLER, Johannes JOCHIMS, Ulrich GROTH, 2002. On alkylideneamidosulfenyl chlorides and 1-Thia-2-azoniaallene salts. In: Helvetica chimica acta. 2002, 85(9), pp. 2627-2635. ISSN 0018-019X. eISSN 1522-2675. Available under: doi: 10.1002/1522-2675(200209)85:9<2627::AID-HLCA2627>3.0.CO;2-H
BibTex
@article{Wirschun2002alkyl-9698,
  year={2002},
  doi={10.1002/1522-2675(200209)85:9<2627::AID-HLCA2627>3.0.CO;2-H},
  title={On alkylideneamidosulfenyl chlorides and 1-Thia-2-azoniaallene salts},
  number={9},
  volume={85},
  issn={0018-019X},
  journal={Helvetica chimica acta},
  pages={2627--2635},
  author={Wirschun, Wolfgang G. and Hitzler, Martin G. and Jochims, Johannes and Groth, Ulrich}
}
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