CNDO/2 investigation of the participation of epoxide rings in conjugation

Furman, E.G.; Meleshevich, A.P.

doi:10.1007/bf00524021

Cited by 2 publications

(1 citation statement)

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“…As well, it has been proposed (39) that elongation of acetal C-0 bonds by hydrogen bonding may result in contraction of adjacent C-0 and C-C bonds. The effect of unsaturated (40)(41)(42)(43)(44)(45)(46) and electronegative (10, 13, 40, 45-52) substituents on the bond lengths of threemembered rings has been investigated extensively. In alicyclic systems T-accepting substituents (40,42,46) tend to shorten the distal bond and lengthen the vicinal bonds of the ring whereas fluoro, 0x0, and methylene groups (43,46,48,51,52) exert the opposite effect.…”

Section: Resultsmentioning

confidence: 99%

X-Ray structure determination of 1,2-anhydro-3,4:5,6-di-O-isopropylidene-1-C-nitro-D-mannitol

Szarek¹,

Hay²,

Sood³

et al. 1988

Can. J. Chem.

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The structure of the major product of the reaction of 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-l-C-nitro-~-arabino-hex-1-enitol with 30% hydrogen peroxide and aqueous sodium hydrogencarbonate has been confirmed by X-ray crystallography to be that of 1,2-anhydro-3,4:5,6-di-0-isopropylidene-1 C-no-D-mannitol (2). The crystal structure of 2, C 12H 19N07, is orthorhombic, P212121, with cell dimensions a = 10.269(3), b = 15.115(7), c = 9.295(8) A, and Z = 4. The calculated density is D, = 1.336 gcm-3. The structure was solved by direct methods and refined to a residual R = 0.052. ' The molecule has a 2G-conformation having bond lengths and angles in agreement with those observed in related structures, except for the C(1)-C(2), C(2)-C(3), and O(2N)-N bond distances which were found to be unusually small. [Traduit par la revue]

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