Advances in Carbohydrate Chemistry, Vol. 12 by Melville L. Wolfrom (ed.), R. Stuart Tipson (ed.)

By Melville L. Wolfrom (ed.), R. Stuart Tipson (ed.)

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This particular mode in cyclohexane was forbidden in the infrared region because of the symmetry of the molecule. Tetrahydropyran, on the other hand, should exhibit an absorption due to this vibration. Since the band at 813 cm.? 2~ The antisymmetrical C-0-C vibration was closely associated with the ring stretching mode of tetrahydropyran (see Fig. 4, B). Beckett, K. S. Pitzer and R, Spitzer, J . A m . Chem. ,69,2488 (1947). A. Ramsay, Proe. Roy. (London), A190, 562 (1947). (26) D. (27) 0. Hassel and B.

I1. The Individual Acids . . . . . . . . . . . . . . . . . . . 1. DL-Lactic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2. D L - ( ~ ,4-Dihydroxybutyric Acid) . . . . . . . . . . . . . . . . . . . a . Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . . .............................. 3. ~~-[2,4-Dihydroxy2-(hydroxymethy1)butyric Acid] . . . .

I11 . Mechanism of Formation of Saccharinic Acids . . . . . . . . . . . . . . 1. The Fragment-recombination Mechanism of Kiliani and Windaus . . . 2 . The Isomerication Mechanism of Nef ................................. . . 35 36 38 38 38 38 39 40 40 40 41 41 41 42 43 43 44 46 47 48 48 49 51 52 52 53 54 55 55 56 59 59 60 61 61 62 62 62 63 36 JOHN C. SOWDEN 3. The Ionic Mechanism of Isbell.. 4. Saccharinic Acids from Substituted Sugars.. 5. Fragment Recombination and Saccharinic Acid Formation.

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