By Fumio Toda (auth.), Fumio Toda (eds.)
The nice variety of substrates, response forms, and items provided during this quantity is either excellent and thought-provoking. there are various examples that seem to be excellent for introducing either undergraduate and graduate scholars to the sphere. interpreting all or a part of this quantity, one will be hard-pressed to prevent coming away with fascinating power functions to one's personal learn efforts, really within the components of heterocyclic synthesis, uneven synthesis, and eco-friendly chemistry.
Kenneth M. Doxsee, collage of Oregon, JA0597799, J.AM.CHEM.SOC., vol. 128, no. eight, 2006
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Although 149a did not form an inclusion complex with 10a–c, 149b–f formed inclusion complexes in the ratios indicated in Table 13. Irradiation of these powdered inclusion complexes in a water suspension gave optically active 150b–f in the chemical and optical yields summarized in Table 13 . Optical yields of 150c and 150e,f were very high. In the case of 149e, two kinds of inclusion complexes with the host 10b were formed with the different host–guest ratios 1:1 and 2:1. Interestingly, photoirradiation of the 1:1 Scheme 21 Thermal and Photochemical Reactions in the Solid State 33 Table 13 Photoreaction of 149b–f in their 1:1 inclusion complexes with 10a–c Host 10b 10c 10c 10a 10b 10b 10c 10c Guest 149b 149c 149d 149e 149e 149e 149e 149f Ratio 1:1 2:1 1:1 1:1 1:1 2:1 2:1 1:1 Irradiation time (h) 40 120 143 96 77 48 50 120 Product (–)-150b (+)-150c (+)-150d (+)-150e (–)-150e (+)-150e (+)-150e (–)-150f Yield (%) Optical purity (% ee) 25 41 16 20 50 86 77 72 8 99 52 93 96 98 98 98 and 2:1 complexes gave (–)-150e and (+)-150e, respectively (Table 13).
Miyamoto H, Yasaka S, Takaoka R, Tanaka K, Toda F (2001) Enantiomer 6:51 13. Yoshizawa K, Toyota S, Toda F (2002) Green Chem 4:68 14. Thompson QE (1958) J Am Chem Soc 80:5483 15. Buu-Hoi N, Saint-Ruf G, Loc TB, Xuong ND (1957) J Chem Soc 2593 16. Yoshizawa K, Toyota S, Toda F, Csoeregh I (2003) Green Chem 5:353 17. Nakamatsu S,Yoshizawa K, Toyota S, Toda F, Matijasic I (2003) Org Biomol Chem 1:2231 18. Tanaka K, Takamoto N, Tezuka Y, Kato M, Toda F (2001) Tetrahedron 57:3761 19. Toda F (2000) Eur J Org Chem 1377 20.
Scheme 17 The thermal solid-to-solid cyclization reaction of diallene derivatives also proceeds stereospecifically. Reaction of 1,6-diphenyl-1,6-di(p-tolyl)hexa-2,4diyne-1,6-diol (113) with HBr gave meso- (114) and rac-3,4-dibromo-1,6-di- phenyl-1,6-di(p-tolyl)hexa-1,2,4,5-tetraene (118). Heating colorless crystals of 114 at 150 °C for 1 h gave in,out-1,2-dibromo-3,4-bis(phenyl-p-tolylmethylene)cyclobutene (117) in quantitative yield [19, 20] (Scheme 18). Similarly, Thermal and Photochemical Reactions in the Solid State 27 Scheme 18 heating colorless crystals of 118 at 150 °C for 1 h gave the in,in- (121) and out,out-isomers (122) of 117 in a 1:1 ratio (Scheme 19).