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Reactivity of Tri‐ tert ‐butylazete
Author(s) -
Vogelbacher Uwe Josef,
Ledermann Martin,
Schach Thomas,
Michels Gisbert,
Hees Udo,
Regitz Manfred
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198802721
Subject(s) - diazomethane , chemistry , cycloaddition , adduct , cyclopentadiene , steric effects , bicyclic molecule , reactivity (psychology) , medicinal chemistry , ketone , hydrolysis , dimethyl acetylenedicarboxylate , acetylenedicarboxylate , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The first kinetically stabilized azete, the title compound 1, is sensitive toward oxidation (→ formation of the dioxetane 2 ) and undergoes hydrolysis to the β‐imino ketone 3 . Sterically nondemanding cycloaddition partners such as cyclopentadiene or diazomethane (CH 2 N 2 ) (→ formation of the adduct 4 ) attack at C‐2/C‐3, whereas those with bulky groups such as acetylenedicarboxylate esters or tert ‐butylphosphaacetylene (PC t Bu) (→ formation of the bicyclic compound 5 ) react at N‐1/C‐4.
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