Premium
Isomerization versus Decarboxylation of Protonated Oxetanone: Comparison between Experimental Results and Theoretical Calculations
Author(s) -
Asensio Gregorio,
Miranda Miguel A.,
PerezPrieto Julia,
Sabater Maria J.,
SimóonFuentes Antonio
Publication year - 1990
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.199011461
Subject(s) - protonation , isomerization , decarboxylation , chemistry , sulfuric acid , ion , carbenium ion , photochemistry , ethylene , computational chemistry , medicinal chemistry , organic chemistry , catalysis
In concentrated sulfuric acid, protonated 2‐oxetanone I H ⊕ behaves other than theoretically predicted. Instead of furnishing ethylene via cleavage of protonated carbon dioxide it isomerizes to the carbenium ion 2 H ⊕ , which is in equilibrium with protonated acrylic acid. This proposed mechanism is supported by investigations with the 4‐ t Bu analogue of 1 H ; in this case the carbenium ion analogous to 2 H ⊕ rearranges with methyl group migration leading to 3 H ⊕ as product.