Ring-transformations of bis(imino)thietanes
✍ Scribed by Gerrit L'abbé; Jean-Paul Dekerk; Hichel Mahy
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 2010
- Weight
- 112 KB
- Volume
- 89
- Category
- Article
- ISSN
- 0037-9646
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✦ Synopsis
Bis(imin0)thietanes 1 are accessible by two methods developed in our laboratory: (i) (3 + 1)-cycloadditions of N-sulfonyl substituted thiiranimines with isonitriles, and (ii) ( 2 + 2)-cycloadditions of sulfonyl isothiocyanates with ketenimines.' An interesting feature of 1 is the presence of a thioimidate function adjacent to an extra imine function which offers the possibility of carrying out ring-transformation reactions as shown below.
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## Abstract For Abstract see ChemInform Abstract in Full Text.
In one of the rare published examples on the title reaction, Cook and coworkers' reported on the Dimroth rearrangement2 of the 5-aminothiazole 1 to the dithiohydantoin 2 followed by mild oxidation to an orange product (mp 270") having structure 2. We have re-examined this reaction and have come to d