Stereochemistry of cyclic compounds

Kucherov, V. F.; Shabanov, A. L.; Onyshchenko, Artur

doi:10.1007/bf01134721

Russ Chem Bull

1963

DOI: 10.1007/bf01134721

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Stereochemistry of cyclic compounds

V. F. Kucherov

A. L. Shabanov

Artur Onyshchenko

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1976

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“…Soc.. 72, 5512(1950). (22) A similar procedure utilizing potassium ierf-butoxide in Et20 at 0 °C was kindly provided by Dr. W. Lever.…”

mentioning

confidence: 99%

Proton magnetic resonance studies of sym-oxepin oxide

Haas¹,

Rastetter²

1976

J. Am. Chem. Soc.

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syw-oxepin oxide (1) in aprotic solvents (CDCI3, CH2CI2, CD2CI2, THF, or CH3CN) with catalytic amounts of MeSOsH led within seconds to the generation of 13. In CDCI3 the addition of MeSC^H (0.1 mol %) catalyzes the quantitative ( NMR) rearrangement of 1 to 13: ir (CDC13) 1725, 1680, 1620, 1260 cm-'; NMR (CDC13, 100 MHz) 9.51 (1 H, d), 6.50 (2 H, m), 4.90 (2 H, m), 3.64 (1 H, m); uv (CH3CN) Xmax 246 (e 590), 310 (110); mass spectrum (70 eV) m/e parent 110, base 81. Exact mass of p-nitrophenylhydrazone: caled forC12Hi,N303, 245.0800; found, 245.0797. Reduction of 13 to 4-Hydroxymethyltetrahydropyran (15). The catalytic reduction of 13 to 4-hydroxymethyltetrahydropyran (15) was achieved in THF-EtOH over Raney nickel catalyst. The catalyst was prepared as for the reduction of 1 to 14, except that the metal was both washed and stored under EtOH rather than THF.

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“…Soc.. 72, 5512(1950). (22) A similar procedure utilizing potassium ierf-butoxide in Et20 at 0 °C was kindly provided by Dr. W. Lever.…”

mentioning

confidence: 99%

Proton magnetic resonance studies of sym-oxepin oxide

Haas¹,

Rastetter²

1976

J. Am. Chem. Soc.

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Stereochemistry of cyclic compounds

Cited by 1 publication

References 2 publications

Proton magnetic resonance studies of sym-oxepin oxide

Proton magnetic resonance studies of sym-oxepin oxide

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