Journal of the Chemical Society. Perkin transactions II p. 971 - 982 (1985)
Update date:2022-07-30
Topics:
Freer, Andrew A.
MacAlpine, Derek K.
Peacock, Judith A.
Porte, Andrew L.
The stereochemistries of caryophyllene nitrosite (3) and dinitrocaryophyllene (5) have been determined by X-ray analyses of their crystal structures.Crystallographic data are: caryophyllene nitrosite, a = 6.476(4), b = 13.199(2), c = 18.784(2) Angstroem, Z = 4, space group P212121; dinitrocaryophyllene, a = 6.405(4), b = 12.991(2), c = 9.797(3) Angstroem, β = 93.04(4) deg, Z = 2, space group P21.The molecular conformations are very similar and caryophylene nitrosite forms solid solutions in dinitrocaryophyllene.Irradiation of these solid solutions with red light generates a monoalkyl nitroxide radical (11), in two symmetry-related orientations, whose spin-Halmiltonian parameters and orientations in the unit cell of the dinitrocaryophyllene crystal have been determined by detailed analyses of single-crystal e.p.r. spectra.Photolysis of pure solid caryophyllene nitrosite with red light generates N2, NO, NO2, dinitrocaryophyllene (5), nitro-nitratocaryophyllene (7), isocaryophyllene (6), and 4,8-bismethylene-11,11-dimethyl-5-nitrobicyclo<7.2.0>undecane (8) and its isomers, compounds (9) and (10).Three nitroxide radicals, two of which have been identified as compounds (11) and (15) are also generated.The combination of chemical, X-ray, and spectroscopic evidence enables the steps in the solid photolysis reactions to be unravelled.
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