A nonspectroscopic method to determine the photolytic decomposition pathways of 3-chloro-3-alkyldiazirine: Carbene, diazo and rearrangement in excited state

C-60 acts as a mechanistic probe for the formation of carbene, diazo compound, and for the rearranged product via the excited state in the photolysis of 3-chloro-3-isopropyldiazirine and 3-chloro-3-chloromethyldiazirine. The carbene adds to C-60 to form methanofullerene, whereas the diazo compound adds to C-60 to form fulleroid. The olefin product arises as a result of the rearrangement in the excited state.PT: J; CR: AKASAKA T, 1999, J ORG CHEM, V64, P566 AKASAKA T, 1999, ORG LETT, V1, P1509 AKASAKA T, 2000, J AM CHEM SOC, V122, P7134 ARENAS JF, 2002, J AM CHEM SOC, V124, P1728 BECKE AD, 1988, PHYS REV A, V38, P3098 BECKE AD, 1993, J CHEM PHYS, V98, P5648 BONNEAU R, 1996, J AM CHEM SOC, V118, P3829 BONNEAU R, 1996, J AM CHEM SOC, V118, P7229 BRINKER U, 1994, ADV CARBENE CHEM, V1 BRINKER U, 1998, ADV CARBENE CHEM, V2 FRISCH MJ, 1998, GAUSSIAN 98 GRAHAM WH, 1965, J AM CHEM SOC, V87, P4396 HIRSCH A, 1993, CHEM BER, V126, P1061 JACKSON JE, 1988, J AM CHEM SOC, V110, P595 LAVILLA JA, 1989, J AM CHEM SOC, V111, P6877 LAVILLA JA, 1989, J AM CHEM SOC, V111, P712 LEE C, 1988, PHYS REV B, V37, P785 LIU MTH, 1987, CHEM DIAZIRINES, V1 LIU MTH, 1987, CHEM DIAZIRINES, V2 LIU MTH, 1996, J AM CHEM SOC, V118, P8098 MARTIN N, 1998, CHEM REV, V98, P2527 MODARELLI DA, 1992, J AM CHEM SOC, V114, P7034 PIETRO WJ, 1982, J AM CHEM SOC, V104, P5039 PLATZ MS, 1994, RES CHEM INTERMEDIAT, V20, P175 SCHICK G, 1998, TETRAHEDRON, V54, P4283 WHITE WR, 1992, J ORG CHEM, V57, P2841; NR: 26; TC: 8; J9: J AM CHEM SOC; PG: 4; GA: 582NTSource type: Electronic(1