Isomerization versus Decarboxylation of Protonated Oxetanone: Comparison between Experimental Results and Theoretical Calculations | Zendy

Asensio Gregorio | Zendy; Miranda Miguel A. | Zendy; PerezPrieto Julia | Zendy; Sabater Maria J. | Zendy; SimóonFuentes Antonio | Zendy

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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.

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