By V Ramamurthy; Kirk S Schanze
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Additional info for Organic molecular photochemistry
RH) ( R-R) %yield %yield %yield 2 11 4 9 (HNA 11:! ) tors, superconductors, photoconductors, ferromagnets, and nonlinear optical materials. Recently, their photoreactivities are attracting attention. However, at the time we undertook the study of donor-acceptor crystals involving nitro and cyano acceptors, only a few reports by Desiraju had dealt with the photoreactivity of donor-acceptor crystals . 8 A distance, the 1 : 1 donor-acceptor complex 19a ·19d was found to be photostable (Scheme 22) [49,50].
77 A (C .. 65 A) (Scheme 32). Ph CN h + PhCHCN . CN . NH NCx:q +CN- I o - NC ~ h NCNNH NCm NC - - NC ~NH_ ~ N +H+ oNHNC Ph ! - NC«N I NC Ph + H+ - H(j>H NC . C•NH Ph +H2~ NC~•NH__ NC~CONHz 1;1 0-C=NH NC . 015 M (solvent) hv + NC~ NC 22 CONHz 70% + TCNB trace 18% Product yields ere based on TCNB employed Initially. , for the TCNB/2-MeBzCN pair, see Scheme 33 [59b]. However, the condensation occurred at the methyl group rather than at the cyanomethyl group and formation of biphenyl derivatives corresponding to 25 could not be found.
For the examples in Scheme 37, chiral handles were introduced into a prochichiral amine by salt formation with optically active camphorsulfonic acids . -adamantylacetophenone-p-carboxylate in Scheme 38 was dimorphic. The major photoproduct from needle-shaped crystals had 97% optical purity. The optical purity of the major photoproduct from plate-like crystals was only 12%. This difference in enantiomeric excess was explained by the X-ray structures of the dimorphs. Thus, the adamantylacetophenone anion in the needle crystals adopts a single homochiral conformation, whereas in the plate form, the anion exists in both conformational chiralities .