TY - JOUR
T1 - Photochemistry of bridged cycloheptadienes. Multiplicity dependent pericyclic rearrangements of excited bicyclo[4.2.1]nona-2,4-diene-7,7,8,8-tetracarbonitrile
AU - Goldschmidt, Zeev
AU - Genizi, Elisheva
PY - 1987
Y1 - 1987
N2 - Bicyclo[4.2.1]nona-2,4-diene-7,7,8,8-tetracarbonitrile rearranges selectively under direct irradiation in acetonitrile to tricyclo[3.2.2.02,4]non-6-ene-8,8,9,9-tetracarbonitrile, and upon acetone sensitization to bicyclo[3.2.2]nona-2,6-diene-8,8,9,9-tetracarbonitrile. Both products are derived from sigma bond cleavage, in contrast to the parent unsubstituted diene where only the π-bonds react.
AB - Bicyclo[4.2.1]nona-2,4-diene-7,7,8,8-tetracarbonitrile rearranges selectively under direct irradiation in acetonitrile to tricyclo[3.2.2.02,4]non-6-ene-8,8,9,9-tetracarbonitrile, and upon acetone sensitization to bicyclo[3.2.2]nona-2,6-diene-8,8,9,9-tetracarbonitrile. Both products are derived from sigma bond cleavage, in contrast to the parent unsubstituted diene where only the π-bonds react.
UR - http://www.scopus.com/inward/record.url?scp=45949123203&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)96647-4
DO - 10.1016/S0040-4039(00)96647-4
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AN - SCOPUS:45949123203
SN - 0040-4039
VL - 28
SP - 4867
EP - 4870
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 41
ER -