Reactions of aziridines with dimethylacetylene dicarboxylate
β Scribed by Albert Padwa; Lewis Hamilton
- Book ID
- 104212692
- Publisher
- Elsevier Science
- Year
- 1965
- Tongue
- French
- Weight
- 175 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
Photochemical cycloaddition reactions of acetylene esters and fused ring heteroaromatic compounds of the general structure (I) have been under extensive investigation in our laboratories.lo3 Cur results demonstrate that sensitized photocycloaddition to benzo(b)thiophene X=O,S,N-R; R=alkyl and many o
## Abstract Dimethyl 3β[(4βnitro)phenyl]aziridineβ2,2βdicarboxylate (3a) represents a new, photochromic aziridine. 3a and related aziridines undergo cycloadditions with dipolarophiles to form fiveβmembered heterocycles and react with nucleophiles with cleavage of the C^2^ο£ΏC^3^ bond.
A new reactibn involving carbon-carbon bond cleavage of the aziridine ring has been observed. Refluxing of 1, 2, J-triphenylaziridine(') (I) with diethylacetylene dicarboxylate in toluene for eleven hours forms 1,2,5-triphenyl-3,4-dicarbethoxy-3-pyrroline(II) in 98% vield. I Recrystallization from e