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[2.2.1.0^2,6]heptane, C₁₄H₁₃ClN₂O₄S

Abstract

MARIA PRZYBYLSKA and DENNIS G . GARRATT. Can. J. Chem. 59,658 (1981). l-Chloromethyl-3-endo-(2',4'-dinitrophenylthio)tricyclo[2.2.1.02~6]heptane, C14H,,CIN204S, crystallizes in space group P2,la with unit cell dimensions a = 12.785(2), b = 10.653(1), c = 11.061(1) A, $ = 101.5ql)q 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. Ilhept-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 C-H...O bonds. Chem. 59,658(1981). L e chloromtthyl-1 (dinitro-2',4' phknylthio) 3-endo tricycl0