Cation radical pericyclic reactions: Cyclopropanation | Zendy

Bauld Nathan L. | Zendy; Stufflebeme Gary W. | Zendy; Lorenz Kurt T. | Zendy

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Cation radical pericyclic reactions: Cyclopropanation

Author(s) -

Bauld Nathan L.,

Stufflebeme Gary W.,

Lorenz Kurt T.

Publication year - 1989

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.610020802

Subject(s) - cyclopropanation , pericyclic reaction , chemistry , ethyl diazoacetate , cyclopropane , regioselectivity , carbene , conjugated system , organic chemistry , photochemistry , medicinal chemistry , catalysis , ring (chemistry) , polymer

Triarylaminium salts smoothly catalyze the cyclopropanation of dienes, styrenes and tetrasubstituted alkenes by ethyl diazoacetate. The reactions are regioselective and, in the case of additions to conjugated dienes, cyclopropane‐periselective. A cation radical chain mechanism involving carbene transfer from ethyl diazoacetate to a substrate cation radical is proposed.

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