Ein Cyclobutadiencarboxylat als Hetero-1,3-dien bei Diels-Alder-Reaktionen mit 2H-Azirinen

✍ Scribed by Regitz, Manfred ;Michels, Gisbert

• Publisher: Wiley (John Wiley & Sons)
• Year: 1990
• Tongue: English
• Weight: 746 KB
• Volume: 123
• Category: Article
• ISSN: 0009-2940
• DOI: 10.1002/cber.19901230444

✦ Synopsis

Antiaromatic Compounds, 26 – A Cyclobutadienecarboxylate as a Hetero‐1,3‐diene in Diels‐Alder Reactions with 2__H__‐Azirines

The cyclobutadienecarboxylic ester 1 adds 2H‐azirines (2a‐1) to yield the oxaazatricyclic compounds 4a‐f. Under thermolysis conditions cleavage of isobutylene and formation of tricyclic ketones occurs (4a, c–e → 7a–d). The Dear pyridone 11 arises from the photolysis of 7a. The structures of compounds 4b and 11 are confirmed by X‐ray crystal structure analyses.