TODA Solid State Reaction

Organic Solid State Reactions Volume Editor Toda, F. 

Toda F (ed) (2000) Organic Solid-State Reactions. Kluwer, Dordrecht Toda F, Bishop R (eds) (2004) Separations and Reactions in Organic Supramolecular Chemistry. WUey, New York... 

Garcia-Garibay M, Scheffer JR, Trotter J, Wireko F (1989) J Am Chem Soc 111 4985 Reviews (a) Sdcamoto M (1997) Chem Eur J 3 684 (b) Sakamoto M (2004) In Inoue Y, RamamurthyV (eds) Chiral photochemistry. Marcel Dekker, New York, chap 11 (in press) Toda F, Tan a K, Miyamoto H (2001) In Ramamurthy V, Schanze KS (eds) Molecular and supramolecular photochemistry, vol 8. Marcel Dekker, New York, chap 6 Tanaka K, Toda F (2002) In Toda F (ed) Organic solid-state reactions. Kluwer,p 109 (a) Toda F, Tanaka K (1986) J Chem Soc Chem Common 1429 (b) Toda F, Tanaka K,Yagi M (1987) Tetrahedron 43 1493... 

Toda et al. reported that the topotactic and enantioselective photodimerization of coumarin and thiocoumarin takes place in single crystals without significant molecular rearrangements [49]. Molecular motion needs to be called upon to explain the photochemically activated cycloaddition reaction of 2-benzyl-5-benzylidenecyclopentanone. The dimer molecules, once formed, move smoothly in the reactant crystal to form the product crystal [50]. Harris et al. investigated the reactivity of 10-hydroxy-10,9-boroxophenanthrene in the solid state and the mechanism of the solid-state reaction was characterized by both X-ray diffraction and thermal analysis [51]. It was demonstrated that the solution chemistry of 10-hydroxy-10,9-boroxophenanthrene is different from that in the solid state, where it undergoes dimerization and dehydration to form a monohydride derivative. 

Curtin and Paul [56] contributed substantially also to the investigation of intra-solid reactions between crystals. In this context. Ref [57] constitutes, together with the other references quoted throughout, a useful entry in the recent literature of organic solid-state reactions, including those activated mechanochemically [57]. An early application to the preparation of charge-transfer systems was reported by Toda and Miyamoto [58]. 

Kaupp G (2005) Stereoselective thermal sohd-state reactions. In Toda F (ed) (preliminary) Organic solid-state reactions. WUey-VCH, Weinheim, in preparation... 

Toda F (ed) (2002) Organic solid-state reactions. Kluwer, Dordrecht... 

K. Tanaka and F. Toda in Organic Solid State Reactions ed. by F. Toda, Kluwer, Dordrecht, The Netherlands, 2002, pp. 1-46 (thermal reactions) and pp. 109-158 (photoreactions). 

This solid-state reaction was discovered by Aoyama etal. and subsequently studied in more detail by Toda etal. Aoyama, H., Hasegawa, T., and Omote, Y. (1979) Solid state photochemistry of jV,jV-dialkyl-ct-oxoamides. Type II reactions in the crystalline state, J. Am. Chem. Soc., 101, 5343-5347. 

Toda F, ed. Organic Solid-State Reactions. Kluwer Academic, 2002. 

Sivaguru J, Shailaja J, Uppili S, Ponchot K, Joy A, Arunkumar N, Ramamurthy, V. In Toda F, ed. Organic Solid-State Reactions. Kluwer Academic, 2002 159-188. 

F. Toda, Solid State Organic Chemistry Efficient Reactions, Remarkable Yields, and Stereoselectivity , Acc. Chem. Res., 28,480 (1995)... 

F. Toda, Solid state organic chemistry efficient reactions, remarkable yields and stereoselectivity, Acc. 

Another use of TADDOL inclusion compounds is to carry out a solid-state reaction with a TADDOL crystal containing an achiral guest molecule, such that the latter is converted to a chiral product. There are again numerous highly successful applications of this procedure by the Toda group [50]. Especially intriguing are enantioselective photoreactions with inter- and intramolecular C,C-bond formation, for which three examples are shown in Scheme 8. 

Komatsu K. Organic solid state reactions. In Toda F, editor. Topics in current chemistry, vol. 254. Berlin Springer 2005. p. 185-206. Wang G-W. in Encyclopedia of Nanoscience and Nanotechnology, vol. 3, (Nalwa HS ed.), American Scientific, Stevenson Ranch, 2004, pp. 557-65. 

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