An improved and general method for the synthesis of α,β-unsaturated oximes from phosphine oxide allenes

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1289-1292

  Palacios, Francisco ^a   Aparicio, Domitila ^a   De Los Santos, Jesús M ^a   Rodríguez, Encina ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; OXIME DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030019960     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02376-3     Document Type: Article

References (47)

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36. While we were developing the experimental work there appeared a very specific example of Wittig olefination of phenanthren-9-one derivatives with stabilized phosphorus ylides for the synthesis of methoxyimino phenanthren-ylidenes14. However, in this reaction the carbon-carbon double bond formation involves the use of functionalized carbonyl compounds containing the oxime group.
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38. 4, 120 MHz) δ 28.4 and 28.7 (syn- and anti-isomers) ppm.
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41. Levy, G. C.; Nelson G. L. J.Am. Chem. Soc. 1972, 94, 4897. Hawkes, G. E.; Herwig, K.; Roberts, J. D. J. Org. Chem. 1974, 39, 1017. Geneste, P.; Durand, R.; Kamenda, J. M.; Beirbeok, H.; Martino, R.; Saunders, J. R. Can. J. Chem. 1978, 56, 1940. Allen, M.; Roberts, J. D. Can. J. Chem. 1981, 59, 451. Gordon, M. S.; Scriba, S. A.; Kramer, J. G. J. Org. Chem. 1984, 49, 97.
42. Levy, G. C.; Nelson G. L. J.Am. Chem. Soc. 1972, 94, 4897. Hawkes, G. E.; Herwig, K.; Roberts, J. D. J. Org. Chem. 1974, 39, 1017. Geneste, P.; Durand, R.; Kamenda, J. M.; Beirbeok, H.; Martino, R.; Saunders, J. R. Can. J. Chem. 1978, 56, 1940. Allen, M.; Roberts, J. D. Can. J. Chem. 1981, 59, 451. Gordon, M. S.; Scriba, S. A.; Kramer, J. G. J. Org. Chem. 1984, 49, 97.
43. Levy, G. C.; Nelson G. L. J.Am. Chem. Soc. 1972, 94, 4897. Hawkes, G. E.; Herwig, K.; Roberts, J. D. J. Org. Chem. 1974, 39, 1017. Geneste, P.; Durand, R.; Kamenda, J. M.; Beirbeok, H.; Martino, R.; Saunders, J. R. Can. J. Chem. 1978, 56, 1940. Allen, M.; Roberts, J. D. Can. J. Chem. 1981, 59, 451. Gordon, M. S.; Scriba, S. A.; Kramer, J. G. J. Org. Chem. 1984, 49, 97.
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46. In the case of 2a and 2b two equivalents of methyl lithium as base were used, while in the case of the silyl oximes 2e and 2d only one equivalent of methyl lithium was used.
47. 2), 120.7 and 128.3 (syn- and anti-HC=), 135.2 and 139.3 (anti- and syn-=CH), 153.1 and 156.3 (syn- and anti-C=N) ppm.