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The Thermal 2 + 2-Addition of N-(2-Phenylallyl), N-(3-phenylally)-toluenesulfonamide: Stereochemical and kinetic evidence for a diradical intermediate

✍ Scribed by Wolfgang Oppolzer

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

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✦ Synopsis

Abstract

Durch Thermolyse der trans‐ und cis‐Bis‐styryl Derivate 1a und 1b erhält man unabhängig von der Konfiguration des Ausgangsmaterials die Produkte 2 und 3 im gleichen Verhältnis. Die Verbindungen 1a, 2 und 3 lassen sich unter den Reaktionsbedingungen ineinander überführen. Diese Resultate sprechen für einen reversiblen Cycloadditionsprozess unter Beteiligung des diradikalischen Zwischenproduktes 4. Eine der Addukt‐Bildung vorgelagerte rasche cis/trans‐Isomerisierung 1b → 1a verläuft offensichtlich über das gleiche Diradikal. Übereinstimmungsgemäss erfolgt die cis/trans‐Isomerisierung des Mono‐styryl Derivates 5 zu 6 wesentlich langsamer als die Isomerisierung 1b → 1a.

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