Download Organic Solid State Reactions: -/- by Fumio Toda (auth.), Fumio Toda (eds.) PDF

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 [33]. 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).

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