Fiesers' Reagents for Organic Synthesis, Volume 20 by Tse-Lok Ho

By Tse-Lok Ho

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Japan 17, 281 (1942) 9 2 SA DES MANUFACTURES DES GLACES ET PRODUITS CHIMIQUES DE SAINT-GOBAIN, CHAUNY & CIREY, Brit. Pat. 792,309; Chem. Abstr. 5 2 , 17805 (1958) 93 STELiou, K. a n d MRANI, M . , / . Am. chem. Soc. E. , J. Am. chem. Soc. 6 9 , 2692 (1947) 95 HAYASHi, K . , iYODA, J . a n d SHIIHARA, L , / . organometal. Chem. 10, 81 (1967) 96 iTOi, K . , Jap. Pat. 68,12,336; Chem. Abstr. 7 0 , 37923 (1969) 97 LAHOURNERE, J . C . a n d VALADE, J . , J. organometal. Chem. 2 2 , C 3 (1970) 98 ALBERT, H .

IYODA, J . a n d SHIIHARA, L , / . organometal. Chem. 10, 81 (1967) 96 iTOi, K . , Jap. Pat. 68,12,336; Chem. Abstr. 7 0 , 37923 (1969) 97 LAHOURNERE, J . C . a n d VALADE, J . , J. organometal. Chem. 2 2 , C 3 (1970) 98 ALBERT, H . j . a n d NEUMANN, W . P . κ. a n d KUIVILA, H . G . , Chemy Ind. , KUIVILA, H . G . , SIMON, R. , J. Am. chem. Soc. , NESMEYANOV, A . N . , Chem. Ber. 6 9 , 1639 (1936) 102 KRAUSE, E. a n d BECKER, R . , Chem. Ber. , SATO, Y. a n d NIWA, M . , Yakugaku ZasshiW, 59 (1970); Chem.

On the other hand, from a synthetic point of view, a change in tin hydride concentration drives the reaction towards R ^ or R2H. Broadly, a high concentration in tin hydride favours RXH, while a low concentration favours R2H. Moreover, the hydrogen transfer rate is a function of the nature of the tin hydride and is greater for triphenyl- than for tributyl-tin hydride5. In the following presentation, emphasis is put on the preparative aspects of the free-radical rearrangements and fragmentations which have been induced by organotin hydrides.

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