Canadian Journal of Chemistry p. 1657 - 1663 (1982)
Update date:2022-08-03
Topics:
Akhtar, Ikbal A.
McCullough, John J.
Vaitekunas, Susan
Faggiani, Romolo
Lock, Colin J. L.
Irradiation of 2-cyanobicyclo<2.2.1>hept-2-ene (2-cyanonorbornene, 4) in hexane, with the full arc of a mercury vapour lamp, gives the rearrangement products 1-cyanobicyclo<4.1.0>hept-2-ene 5 and 7-cyanotricyclo<4.1.0.03,7>heptane 6 in the ratio 20:1.These products were separated by preparative vpc.The structure of the major product 5 was determined by single crystal X-ray analysis.Reduction of 5 with lithium aluminum hydride gave the corresponding primary amine, which was converted to the p-bomobenzenesulfonamide 9, mp 150-151 deg C, which gave single crystals from ethanol-water.The crystal and molecular structures are described.The minor product 6 was hydrogenated to give 7-cyanobicyclo<2.2.1>heptane.Formation of 5 and 6 may involve concerted ?2s + ?2s and ?2a + ?2a processes respectively, which are photochemically allowed.
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(1982)Doi:10.1021/jm00355a012
(1983)Doi:10.1055/s-1984-30813
(1984)Doi:10.1016/0039-128X(82)90129-5
(1982)Doi:10.1021/ja00389a054
(1982)Doi:10.1016/S0040-4039(00)87419-5
(1982)
