Cycloaddition of Acyclic Nitrones with Phenyl Isocyanate: Synthesis and Ring-Opening Reactions of 1,2,4-Oxadiazolidin-5-ones.
✍ Scribed by Necdet Coskun; Aydin Parlar
- Publisher
- John Wiley and Sons
- Year
- 2006
- Weight
- 14 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0931-7597
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In a continuing study of cycloaddition reactions involving cyclopropane ring-containing systems (1) we have investigated the reactions of vinylcyclopropane and some substituted vinylcyclopropanes with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and chlorosulfonylisocyanate (CSI).
5-Imino-1,2,4-thiadiazolidin-3-ones 1 react with compounds alkylidene-1,2,4-dithiazolidines 12 are formed. The reaction products with enamines undergo hydrolysis and elimination containing electron-rich double bonds such as enamines and ester enolates to afford the 2-iminothiazolidines 3, 4, and 10
Addition of dimethyl phosphonate to acetaldol gives a 3 : 7 mixture of diastereomeric dimethyl (1,3-dihydroxybutyl)phosphonates 3 and 4. The relative configurations at C-I and C-3 in these diols were established by the 13C NMR data of their 0-benzylidene derivatives. Axial preference-for the dimetho