Ring-transformation equilibrium with participation of π-bonded S in an isothiazole system. Synthesis of non-ring-transformed 5-(2-aminovinyl)isothiazole derivative via 1,3-silyl group shift
✍ Scribed by Katsuo Ohkata; Yoshihiko Ohyama; Yuko Watanabe; Kin-ya Akiba
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 252 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
In the course of our investigations on bond switch at hypervalent sulfur atom, there were found a reversible ring-transformation (l-d@l-B)l and an irreversible ring-transformation (2-d-+2-B),2 depending on symmetrical and unsymmetrical nature of the interconverting sulfur containing heterocycles. Recently, we observed also such an equilibrium in 5-(2-aminovinyl) isothiazole system (3-gs3-B) under basic conditions for synthesis.
3
In this communication, we wish to describe a synthesis of N-silylated derivatives of A, 2, and the related oxygen analogue, i.e.,z,R, and2, and of pure compounds of d-form ofAby means of desilylation of Lwith tetra-n-butylammonium fluoride (TBAF).