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- W2054293823 abstract "The AlH 2 Cl hydrogenolysis of ether solutions of 2-alkoxytetrahydrofurans in which the alkoxy group is either CH 3 O, C 2 H 5 O, i-C 3 H 7 O, or t-C 4 H 9 O, gives only those products resulting from ring C—O bond cleavage. However, substituents at C-5 of 2-methoxytetrahydrofuran exert a strong effect on the ratio of ring to exo C—O bond cleavage. Thus, alkyl (electron donor) groups at C-5 promote an increase in the amount of exo cleavage, the proportion increasing from 62.5 to 100% as the C-5 alkyl group is changed from CH 3 to t-C 4 H 9 . In contrast, electron withdrawing substituents, CH 3 OCH 2 — and C 6 H 5 , at C-5 favor ring cleavage to the extent of 93 and 84% respectively.The results are interpreted in terms of the influence that these substituents exert through their electronic properties on the relative ease of attainment of the transition state leading to either ring C—O or exo C—O bond cleavage. However, evidence is provided to show that the bulk steric effect of these substituents also controls, though to a minor extent, the proportion of ring to exo cleavage." @default.
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- W2054293823 date "1972-05-15" @default.
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- W2054293823 title "The Influence of the 2-Alkoxy Group and of C-5 Substituents on the Direction of Reductive Cleavage of 2-Alkoxytetrahydrofurans by AlH2Cl in Ether Solution" @default.
- W2054293823 doi "https://doi.org/10.1139/v72-238" @default.
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