𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Photochemische Cycloadditionen von 3-Phenyl-2H-azirinen an Carbonsäurechloride. 35. Mitteilung über Photoreaktionen

✍ Scribed by Ursula Schmid; Paul Gilgen; Heinz Heimgartner; Hans-Jürgen Hansen; Hans Schmid

Publisher
John Wiley and Sons
Year
1974
Tongue
German
Weight
731 KB
Volume
57
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Irradiation of 2, 3‐diphenyl‐2__H__‐azirine (1a) and 1‐azido‐1‐phenyl‐propene, the precursor of 2‐methyl‐3‐phenyl‐2__H__‐azirine (1b), in benzene, with a high pressure mercury lamp (pyrex filter) in the presence of acid chlorides yields the oxazoles 5a–d (Scheme 2). Photolysis of 2, 2‐dimethyl‐3‐phenyl‐2__H__‐azirine (1c) under the same conditions gives after methanolysis the 5‐methoxy‐2, 2‐dimethyl‐4‐phenyl‐3‐oxazolines 7a, b, d, while hydrolysis of the reaction mixture leads to the formation of the 1, 2‐diketones 8a, c, d (Scheme 4). The suggested reaction path for all these reactions is a 1, 3‐dipolar cycloaddition of the photochemically generated benzonitrilemethylides 2 to the carbonyl double bond of the acid chlorides to give the intermediates 4, followed by either elimination of hydrogen chloride or solvolysis (Schemes 2 and 4).

Irradiation of 1c in the presence of acetic acid anhydride leads via the intermediate 9 to the 5‐hydroxy‐3‐oxazoline 10 and the 5‐methylidene‐3‐oxazoline 11 (Scheme 5).

📜 SIMILAR VOLUMES

Photochemische Cycloadditionen von 3-phe
Photochemische Cycloadditionen von 3-phenyl-2h-azirinen mit Aldehyden. 31. Mitteilung über Photoreaktionen
✍ Heinz Giezendanner; Heinz Heimgartner; Barry Jackson; Tammo Winkler; Hans-Jürgen 📂 Article 📅 1973 🏛 John Wiley and Sons 🌐 German ⚖ 860 KB

## Abstract Experiments concerning the photochemical condensation of 3‐phenyl‐2__H__‐azirines **1** with aliphatic and aromatic aldehydes to 3‐oxazolines **4** are fully described (__cf__. scheme **1**). Photochemically nitrile methylides of type 2 are first formed, which then very quickly react th

Photochemische Cycloadditionen von 3-Phe
Photochemische Cycloadditionen von 3-Phenyl-2H-azirinen mit Triphenyl-vinylphosphoniumbromid. 36. Mitteilung über Photoreaktionen
✍ Nikolas Gakis; Heinz Heimgartner; Hans Schmid 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 German ⚖ 327 KB

## 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 tha

Photoinduzierte Cycloadditionen von alip
Photoinduzierte Cycloadditionen von aliphatischen 2H-Azirinen. 37. Mitteilung über Photoreaktionen
✍ Alexander Orahovats; Heinz Heimgartner; Hans Schmid; Willy Heinzelmann 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 German ⚖ 563 KB

The purely aliphatic 2,3‐dipropyl‐2__H__‐azirine (**1**) reacts on irradiation with a mercury high‐pressure lamp through a Vycor filter with methyl trifluoroacetate or acetone to form 3‐oxazolines **3a, b** (65%) resp. **4** (14%) (__Scheme 1__). 9‐Azabicyclo[6.1.0]non‐1(9)‐ene (**5**) on irradiatio

Photochemische Cycloadditionen von 3-Phe
Photochemische Cycloadditionen von 3-Phenyl-2H-azirinen mit kumulierten Doppelbindungen. Vorläufige Mitteilung
✍ B. Jackson; N. Gakis; M. Märky; H.-J. Hansen; W. von Philipsborn; H. Schmid 📂 Article 📅 1972 🏛 John Wiley and Sons 🌐 German ⚖ 166 KB

## 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-Phe
Photochemische Cycloadditionen von 3-Phenyl-2H-azirinen mit aktivierten Doppelbindungen. Vorläufige Mitteilung
✍ B. Jackson; M. Märky; H.-J. Hansen; H. Schmid 📂 Article 📅 1972 🏛 John Wiley and Sons 🌐 German ⚖ 173 KB 👁 1 views

## 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**

Photoinduzierte 1, 3-dipolare Cycloaddit
Photoinduzierte 1, 3-dipolare Cycloaddition von 3-Phenyl-2H-azirinen an Azodicarbonsäure-diäthylester. 32. Mitteilung über Photoreaktionen
✍ Paul Gilgen; Heinz Heimgartner; Hans Schmid 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 German ⚖ 662 KB

## Abstract Irradiation of 2, 2‐dimethyl‐3‐phenyl‐ (**1a**), 2, 3‐diphenyl‐2__H__‐azirine (**1b**) or the azirine‐precursors 1‐azido‐1‐phenyl‐propene (**2a**) and 1‐azido‐1‐phenyl‐ethylene (**2b**), respectively, in benzene in the presence of azodicarboxylic acid diethylester, yields the correspond