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- W1978005406 abstract "A new di-O-benzylidene derivative of d-arabinose diethyl dithioacetal, obtained by benzylidenation with α,α-dimethoxytoluene, was shown by X-ray crystallography to have the 2,4:3,5-di-O-benzylidene structure. The two O-benzylidene rings are trans-fused, and the CH(SEt)2 group adopts an axial orientation at C-4 of a 2-phenyl-1,3-dioxane ring. The axial group is twisted, and there is some distortion of the chair conformation of the ring. 1H-N.m.r. coupling-constants showed that the conformation is similar in solution. Molecular-mechanics calculations using a modified MM2 program indicated that the distortions are caused by intramolecular interactions. They also suggest that rotation about the bond from the acetal carbon atom to the phenyl ring in 2-phenyl-1,3-dioxanes is not free, as previously calculated. The parallel conformation was calculated to be a minimum, and the perpendicular conformation a saddlepoint 0.95 kcal.mol−1 higher on the potential-energy surface. The 1H- and 13C-n.m.r. parameters of this system and other trans-fused 3,7-diphenyl-2,4,6,8-tetraoxa[4,4]bicyclodecanes do not fit the ranges previously proposed for structural assignment of benzylidene acetals. The ranges have been revised to include this type of compound." @default.
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- W1978005406 date "1987-02-01" @default.
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- W1978005406 title "The crystal structure of 2,4:3,5-di-O-benzylidene-d-arabinose diethyl dithioacetal, and related molecular-mechanics calculations" @default.
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- W1978005406 doi "https://doi.org/10.1016/s0008-6215(00)90213-1" @default.
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