Dehydration induced by intramolecular redox character of a stable allylidenetributylphosphorane

Tetrahedron Letters

Volumn 38, Issue 45, 1997, Pages 7893-7896

  Kawamura, Yasuhiko ^a   Sato, Yoshinori ^a   Horie, Tokunaru ^a   Tsukayama, Masao ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; AMIDE; ESTER; PHOSPHORANE DERIVATIVE; TRIBUTYL PHOSPHATE;

ARTICLE; DEHYDRATION; MOLECULAR STABILITY; OXIDATION REDUCTION REACTION; SYNTHESIS;

EID: 0030731502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10099-5     Document Type: Article

References (25)

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3. (a) Tsunoda, T.; Ozaki, F.; Itô, S. Tetrahedron Lett. 1994, 35, 5081-5082.
4. (b) Tsunoda, T.; Nagaku, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H.; Itô, S. Tetrahedron Lett. 1995, 36, 2531-2534.
5. (c) Tsunoda, T.; Yamamoto, H.; Goda, K.; Itô, S. Tetrahedron Lett. 1996, 37, 2457-2458.
6. (d) Tsunoda, T.; Nagino, C.; Oguri, M.; Itô, S. Tetrahedron Lett. 1996, 37, 2459-2462.
7. (e) Tsunoda, T.; Ozaki, F.; Shirakata, N.; Tamaoka, Y.; Yamamoto, H.; Itô, S. Tetrahedron Lett. 1996, 37, 2463-2466. The P-ylides utilized in these papers are reported as sensitive to air and moisture.
8. Formations of anhydrides in the Mitsunobu reaction: Harvey, P. J.; von Itzstein, M.; Jenkins, I. D. Tetrahedron 1997, 53, 3933-3942, and references cited therein.
9. The Mitsunobu reaction, general: (a) Mitsunobu, O. Synthesis, 1981, 1-28.
10. (b) Hughes, D. L. The Mitsunobu Reaction. In Organic Reactions; Beak, P. et al. Eds.; John Wiley & Sons, Inc.: New York, Vol. 42, 1992; pp. 335-656.
11. 13). A priori, the stereochemistry of 7 is deduced to be s-trans based on a result of the same calculation. Details will be published elsewhere in due course.
12. Compound 1: Johnson, A. W.; LaCount, R. B. Tetrahedron 1960, 9, 130-138.
13. Compound 2c: (a) Brown, G. W.; Cookson, R. C.; Stevens, I. D. R. Tetrahedron Lett. 1964, 1263-1266.
14. 6P: C, 74.45; H, 5.29%, Found: C, 74.16; H, 5.39%. Ylide 2 showed temperature dependent NMR spectra and the analyses are elaborated. Manuscript is now in preparation.
15. 1H NMR and gas chromatography.
16. 14
17. Measurement of pKa values: Flexser, L. A.; Hammett, L. P.; Dingwall, A. J. Am. Chem. Soc. 1935, 57, 2103-2115. It is known that the stable P-ylides, acylmethylenetriphenylphosphoranes, react with acid anhydrides to give more acylated ones, which undergo further transformations upon treatment with alcoholic mineral acid or pyrolysis: Chopard, P. A.; Searle, R. J. G.; Devitt, F. H. J. Org. Chem. 1965, 30, 1015-1019. In the reactions of 2b-e, however, unreacted starting materials were recovered.
18. Measurement of pKa values: Flexser, L. A.; Hammett, L. P.; Dingwall, A. J. Am. Chem. Soc. 1935, 57, 2103-2115. It is known that the stable P-ylides, acylmethylenetriphenylphosphoranes, react with acid anhydrides to give more acylated ones, which undergo further transformations upon treatment with alcoholic mineral acid or pyrolysis: Chopard, P. A.; Searle, R. J. G.; Devitt, F. H. J. Org. Chem. 1965, 30, 1015-1019. In the reactions of 2b-e, however, unreacted starting materials were recovered.
19. 4S: C, 72.54; H, 5.15%, Found: C, 72.31; H, 5.34%. This ylide showed a temperature dependent NMR spectra similar to those of 2. The analyses will be presented elsewhere.
20. (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353-1364.
21. (b) Kaiser, C.; Trost, B. M.; Beeson, J.; Weinstock, J. J. Org. Chem. 1965, 30, 3972-3975.
22. (c) Payne, G. B. J. Org. Chem. 1967, 32, 3351-3355.
23. The pKa of the phosphonium salt of 1 was measured to be 8.0.
24. Stewart, J. J. P.; J. Comput. Chem. 1989, 10, 221-264.
25. McClure reported an analogous ylide transformation to prepare cyanomethylenetriphenylphosphorane from the reaction of ethoxycarbonylmethylenetriphenylphosphorane with acrylonitrile: McClure, J. D.; Tetrahedron Lett. 1967, 2407-2410.