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

G Haufe, MW Tubergen, PJ Kropp

Index: Haufe, Guenter; Tubergen, Mark W.; Kropp, Paul J. Journal of Organic Chemistry, 1991 , vol. 56, # 13 p. 4292 - 4295

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Abstract

Irradiation of cyclononene (7b) and cycloundecene (7d) in pentane afforded cia-bicyclo [4.3. 0] nonane (lob) and cis-bicyclo [6.3. 0] undecane (loa), respectively. Small amounta of the Eragmentation produds 1-undecene (lad) and 1-undecyne (lM) were ale0 obtained from cycloundecene (7d). The photobehavior of the seriea of medium-and large-ring alkenes 7a- e is compared. Aside from E* 2 isomerization, the principal pathway in each case involves ...