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Ein Cyclobutadiencarboxylat als Hetero‐1,3‐dien bei Diels‐Alder‐Reaktionen mit 2H‐Azirinen
Author(s) -
Regitz Manfred,
Michels Gisbert
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230444
Subject(s) - chemistry , thermal decomposition , diels–alder reaction , antiaromaticity , photodissociation , enone , yield (engineering) , cleavage (geology) , crystal structure , isobutylene , medicinal chemistry , stereochemistry , photochemistry , molecule , organic chemistry , catalysis , aromaticity , materials science , polymer , geotechnical engineering , copolymer , fracture (geology) , engineering , metallurgy
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.