TY - JOUR
T1 - [3,5]-sigmatropic shifts in the photochemistry of 1-allyl-naphthalen-2(1H)- ones
AU - Cunningham, Patrick D.
AU - Geraghty, Niall W.A.
AU - Hanly, Noreen M.
AU - McArdle, Patrick J.
PY - 1985
Y1 - 1985
N2 - Although the formation of a 2a,3,4,8b-tetrahydro-1,4-methanocyclobuta[a] naphthalen-2(1H)-one (2) in the photolysis of 1-methyl-1-(prop-2-enyl)- naphthalen-2(1H)-one (5) is confirmed by X-ray crystallography of the corresponding 7-bromo photoproduct (3), the available evidence does not support the previously made suggestion that this occurs via a [3,5]-sigmatropic shift; an alternative mechanism involving an arene-alkene exciplex is suggested.
AB - Although the formation of a 2a,3,4,8b-tetrahydro-1,4-methanocyclobuta[a] naphthalen-2(1H)-one (2) in the photolysis of 1-methyl-1-(prop-2-enyl)- naphthalen-2(1H)-one (5) is confirmed by X-ray crystallography of the corresponding 7-bromo photoproduct (3), the available evidence does not support the previously made suggestion that this occurs via a [3,5]-sigmatropic shift; an alternative mechanism involving an arene-alkene exciplex is suggested.
UR - http://www.scopus.com/inward/record.url?scp=37049107285&partnerID=8YFLogxK
U2 - 10.1039/c39850001698
DO - 10.1039/c39850001698
M3 - Article
SN - 0022-4936
SP - 1698
EP - 1700
JO - Journal of the Chemical Society D: Chemical Communications
JF - Journal of the Chemical Society D: Chemical Communications
IS - 23
ER -