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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 5
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Original Articles

A New Synthesis of α-Methylene Carbinols

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Pages 411-418 | Received 20 Nov 1978, Published online: 06 Dec 2006

References

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  • M. p. 55–56° (ex ether-ligroin); n.m.r. (CDCl3) δ: 3.58 (1 H, d, J = 15 Hz), 3.03 (1 H, d, J = 15 Hz), 2.83 (1 H, narrow m), 2.3–1.9 (2 H, m), 1.9–1.6 (2 H, m), 1.5–1.1 (4 H, m); i.r. (CCl4) 1 325 (s), 1 305 (m), 1 158 (s) cm-1
  • N.m.r. (CDCl3) δ: 4.98 and 4.75 (1 H each, broadened s), 4.1 (1 H, br)
  • Broaddus , C. D. 1968 . Accts. Chem. Res. , 1 : 123
  • Barton , D. H. R. , Da Campos-Neves , A. S. and Cookson , R. C. 1956 . J. Chem. Soc. , : 3500 Epoxidation of 3-methylcholest-2-ene gives almost exclusively the α-epoxide
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  • Kocienski , P. J. , Lythgoe , B. and Ruston , S. J. Org. Chem. , in press
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  • Posner , G. H. and Brunelle , D. J. 1972 . J. Org. Chem. , 37 : 3547 Prepared by the procedure of
  • A pure sample of the α-epoxide12 obtained by fractional crystallization of the mixture from benzene-ligroin had m.p. 173–174°C; [α18D = + 50° (CO. 2, CHCl3); n.m.r. (CDCl3) δ 3.52 and 3.10 (1 H each, AB quartet, J = 14 Hz, PhSO2CH2-), 3.05 (1 H, s, J = 5 Hz, CH-0)
  • This compound gave a satisfactory combustion analysis

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