Transannular reactions of cycloalkenes, cycloalkadienes and cycloalkatrienes. 16. Photocyclization of cyclononene and cycloundecene

Autor:	Paul J. Kropp, Guenter Haufe, M. W. Tubergen
Rok vydání:	1991
Předmět:	Pentane chemistry.chemical_compound Cyclononene chemistry Bicyclic molecule Organic Chemistry Reaction intermediate Nonane Undecane Carbene Isomerization Medicinal chemistry
Zdroj:	The Journal of Organic Chemistry. 56:4292-4295
ISSN:	1520-6904 0022-3263
Popis:	Irradiation of cyclononene and cycloundecene in pentane afforded cis-bicyclo[4.3.0]nonane and cis-bicyclo[6.3.0]undecane, respectively. Small amounts of the fragmentation products 1-undecene and 1-undecyne were also obtained from cycloundecene. The photobehavior of the series of medium- and large-ring alkenes is compared. Aside from E⇄Z isomerization, the principal pathway in each case involves rearrangement of the π,R(3s) excited to a cycloalkylidene intermediate which undergoes predominant, if not exclusive, 1,5-transannular insertion to afford the corresponding cis-bicyclo[n.3.0]alkane
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::19e2ced46bfeccda6b16e6f68fe4f371 https://doi.org/10.1021/jo00013a041 Zobrazit plný text záznamu