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Thermische und photochemisch induzierte intramolekulare, 1,3-dipolare Cycloadditionen von 4-Phenyl-3-(2-allylphenyl)-sydnon. Vorläufige Mitteilung. 53. Mitteilung über Photoreaktionen

✍ Scribed by Hansruedi Meier; Heinz Heimgartner; Hans Schmid

Publisher: John Wiley and Sons
Year: 1977
Tongue: German
Weight: 219 KB
Volume: 60
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19770600333

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✦ Synopsis

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). 9 reacts at room temperature with its potential azomethinimine‐function in an intramolecular [3+2]‐cycloaddition to give the tricyclic compound 11 (Scheme 2). On irradiation, 9 yields the dihydro‐3__H__‐pyrazolo[2,3‐a]indole 10 which probably arises by intramolecular [3+2]‐cycloaddition of the corresponding intermediate nitrilimine.

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Thermisch und photochemisch induzierte intramolekulare, 1,3-dipolare Cycloadditionen von 5-(2-Allyloxyphenyl)-2-phenyltetrazol. Vorläufige Mitteilung. 54 Mitteilung über Photoreaktionen

✍ Hansruedi Meier 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 German ⚖ 206 KB

**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