## Abstract Irradiation of 2‐methyl‐ (**1c**) and __2,2__‐dimethyl‐3‐phenyl‐__2H__‐azirine (**1d**) in benzene solution in the presence of carbon dioxide yields __2__‐methyl‐4‐phenyl‐ (**3c**) and __2,2__‐dimethyl‐4‐phenyl‐3‐oxazolin‐5‐one (**3d**), respectively. Similar cycloadducts are observed (
Photochemische Cycloadditionen von 3-Phenyl-2H-azirinen mit Triphenyl-vinylphosphoniumbromid. 36. Mitteilung über Photoreaktionen
✍ Scribed by Nikolas Gakis; Heinz Heimgartner; Hans Schmid
- Publisher
- John Wiley and Sons
- Year
- 1974
- Tongue
- German
- Weight
- 327 KB
- Volume
- 57
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
On irradiation in acetonitrile 3‐phenyl‐2H‐azirines of type 1 react with triphenyl vinyl phosphonium bromide to form in approximative 50% yield 2H‐indoles of type 4 (Scheme 1). In analogy to other photochemical reactions with 2H‐azirines [2] [3] it is assumed that the photochemically generated dipoles 2 react with the triphenyl vinyl phosphonium salt (Scheme 1). The conversion of 1 to 4 represents a new synthesis for 2H‐pyrroles.
📜 SIMILAR VOLUMES
## Abstract Irradiation of 2‐methyl‐ (**1a**), 2,2‐dimethyl‐ (**1b**) and 2,3‐diphenyl‐2__H__‐azirine (**1c**) in the presence of diethyl mesoxalate yields the corresponding 4‐phenyl‐5,5‐diethoxycarbonyl‐3‐ oxazolines **3a–c**. Similar cycloadducts are observed (cf. **6**) by irradiation of **1b**
**Thermal and photochemically induced intramolecular 1,3‐dipolar cycloaddition reactions of 4‐phenyl‐3‐(2‐allylphenyl)‐sydnone** The title compound **9** was synthesised in the usual way, starting from 2‐allylaniline and ethyl 2‐bromo‐2‐phenylacetate, __via__ the nitrosaminacid **8** (__Scheme 2__)
**Thermal and Photochemically Induced Interamolecular 1,3‐Dipolar Cycloaddition Reactions of 5‐(2‐Allyloxyphenyl)‐2‐phenyltetrazole** The title compound **5** is easily obtained by a recently described procedure (__Scheme 2__). The tetrazole **5** reacts at 165–170° or on irradiation at room temper