Clin Biochem Illustrated Color Text

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84:3516 37. See for example: (a) Jorgensen WL, Severance DL (1990) J. Am. Chem. Soc. 112: 4768; (b) See also ref 47 and 48. 38. See for example: (a) Haselbach E, Vauthey E, Suppan P (1988) Tetrahedron 44: 7335; (b) Jones G II, Moutie N (1988) J. Phys. Chem. 92: 7174; (c) Haselbach E, Jacques P, Pilloud D, Suppan P, Vauthey E (1991) J. Phys. Chem. 95: 7115; (d) Devadoss C, Fessenden RW (1991) J. Phys. Chem. 95: 7523; (e) Angerhofer A, Toporowicz M, Bowman MK, Norris JR, Levanon H (1988) J. Phys.

In benzene erythro/threo selectivity is high, being highest for the relatively basic radical anion of dicyanonaphthalene and lowest for the relatively nonbasic radical anion of thioindigo. The stereochemical preference disappears in acetonitrile if biphenyl is used as a co-sensitizer [108]. These observations are accounted for by radical anion (base) assisted fragmentations, where anti stereochemistry, analogous to that in elimination reactions, is favored. The intramolecular hydrogen bonding in the threo isomers leads to gauche arrangements of the reactive substituents, diminishing the rate of assisted fragmentation [108].

109: 5061; (g) Kroon J, Verhoeven JW, Paddon-Row MN, Oliver AM (1991) Angew. Chem. Int. Ed. Engl. 30: 1358; (h) Warman JM, Smit KJ, de Haas MP, Jonker SA, Paddon-Row MN, Oliver AM, Kroon J, Oevering H, Verhoeven JW (1991) J. Phys. Chem. 95:1979 40. (a) Fox MA (1991) Top. Curr. Chem. 159: 67; (b) Nakabayashi S, Kawai T (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, part B. Elsevier, Amsterdam, p 599; (c) Wasielewski MR (1992) Chem. Rev. 92:435 41. (a) Lymar CV, Parmon VN, Zamarev KI (1991) Top.

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