Paper
The addition of 2,4-dinitrobenzenesulphenyl chloride to 2-methylenebicyclo[2.2.1]hept-5-ene: the crystal structure of 1-chloromethyl-3-endo-(2′,4′-dinitrophenylthio)tricyclo[2.2.1.02,6]heptane, C14H13ClN2O4S
Published Feb 15, 1981 · M. Przybylska, D. Garratt
Canadian Journal of Chemistry
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Abstract
1-Chloromethyl-3-endo-(2′,4′-dinitrophenylthio)tricyclo[2.2.1.02,6]heptane, C14H13ClN2O4S, crystallizes in space group P21/a with unit cell dimensions a = 12.785(2), b = 10.653(1), c = 11.061(1) A, β = 101.54(l)° Z = 4.The structure was solved from Patterson and Fourier maps. The parameters were refined by block-diagonal least-squares to a final R = 0.038 for 2063 observed reflections. The structural data provide unequivocal proof for our earlier ascertainment of configurational-specific exo attack upon the endocyclic double bond of 2-methylenebicyclo[2.2.1]hept-5-ene with homoallylic participation.The molecule is characterized by the presence of an interaction between oxygen of the 2-nitro group and a sulphur atom, and of a weak bifurcated hydrogen bond system involving bonds.
The crystal structure of 1-chloromethyl-3-endo-(2′,4′-dinitrophenylthio)tricyclo[2.2.1.02,6]heptane confirms configurational-specific exo attack on the endocyclic double bond with homoallylic participation.
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