Unusual photochemical behavior of 5-amino-endo-dicyclopentadien-3-ones
Bakkeren FJAD, Schroer F, de Gelder R, Klunder AJH, Zwanenburg B
TETRAHEDRON LETTERS
39 (51): 9527-9530 DEC 17 1998


Abstract:
Irradiation of 5-amino-substituted endo-tricyclo[5.2.1.0(2.6)]deca-4,8-dien-3-ones 3 did not lead to the anticipated [pi(2) + pi(2)]-photocyclization to afford bridgehead 1,3-bishomocubyl amines 4. Instead an unexpected photoreduction of the norbornene C-8-C-9 double bond was observed, which based on D-labelling studies involves a photo-electron transfer process. The desired [pi(2) + pi(2)]-photo-cyclization furnishing 4-amido-substituted 1,3-bishomocubanones 7 could however be effected by N-acylation of the amino function in 3.