By Charles D. Harrington, Archie E. Ruehle
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Sample text
Perhaps, it should also be mentioned that although the t-27 molecules in the double salt t-27 ·en are separated (Ca. 76 A, c~ .. 2 A), they can still undergo photodimerization. As displayed in Scheme 44 [76], irradiation of double salts prepared from anthracene-9-propionic acid (9-AP) with (R,R)- or (S,S)+chxn readily afforded the thermally unstable head-to-head dimer as a sole product rather than the stable head-to-tail dimer which is the predominant photoproduct in solution. In contrast, the homocrystal of 9-AP and the double salt 9-AP·en were photostable in the solid state.
Perhaps, it should also be mentioned that although the t-27 molecules in the double salt t-27 ·en are separated (Ca. 76 A, c~ .. 2 A), they can still undergo photodimerization. As displayed in Scheme 44 [76], irradiation of double salts prepared from anthracene-9-propionic acid (9-AP) with (R,R)- or (S,S)+chxn readily afforded the thermally unstable head-to-head dimer as a sole product rather than the stable head-to-tail dimer which is the predominant photoproduct in solution. In contrast, the homocrystal of 9-AP and the double salt 9-AP·en were photostable in the solid state.
Such a case the prediction of the product stereochemistry on the basis of the crystal structure is not direct. ) the presence of disorder at the ethylene carbons [81]. The former feature is considered to be the clue responsible for the compulsory reaction control. As pictured in Scheme 49, molecules of t-30 are arranged in a syn head-to-head fashion in the layer and are thus suitable for cycloaddition leading to ~-truxinam ide. The latter feature indicates that the ethylene bond moiety of t-30 is particularly susceptible to torsional vibration in the crystal lattice, as was likewise suggested for t-30·pht (Scheme 48).