A vinylcyclobutane substrate designed as a cyclopropylcarbinyl radical probe

Autor:	Ryan M. Bell, Phyllis A. Leber, Carlton W. Christie, Joseph A. Mohrbacher Iii
Rok vydání:	2013
Předmět:	Cyclopropanes Bicyclic molecule Free Radicals Molecular Structure Cyclopropanation Chemistry Diradical Organic Chemistry Substrate (chemistry) Photochemistry Biochemistry Substrate Specificity Kinetics Drug Design Thermodynamics Physical and Theoretical Chemistry Cyclobutanes
Zdroj:	Organicbiomolecular chemistry. 11(13)
ISSN:	1477-0539
Popis:	Appending a spirocyclopropane linkage to bicyclo[3.2.0]hept-2-ene is achieved by selective kinetic cyclopropanation of 6-methylenebicyclo[3.2.0]hept-2-ene. The resultant vinylcyclobutane undergoes [1,3] migration as the dominant thermal process. A minor cyclopropylcarbinyl (CPC) rearrangement product clearly implicates a diradical transition structure. The presence and absence of other potential thermal products have enabled us to construct a detailed mechanistic proposal to account for all viable dynamic processes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9dbc03ed1a41276b8c0262a31566bc30 https://pubmed.ncbi.nlm.nih.gov/23435791 Zobrazit plný text záznamu