Preparation of nitriles from primary alcohols by a new type of oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone and diethyl cyanophosphonate

Chemistry Letters

Volumn 33, Issue 9, 2004, Pages 1192-1193

  Mukaiyama, Teruaki ^a,b   Masutani, Kouta ^a,b   Hagiwara, Yoshiaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIMETHYLBENZOQUINONE; ALCOHOL DERIVATIVE; BENZOQUINONE DERIVATIVE; DIETHYL CYANOPHOSPHONATE; LITHIUM DERIVATIVE; NITRILE; PHOSPHINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYANATION; OXIDATION REDUCTION REACTION; POLYMERIZATION; QUANTUM YIELD;

EID: 9344260243     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1192     Document Type: Article

References (18)

1. a) T. Mukaiyama, I. Kuwajima, and Z. Suzuki, J. Org. Chem., 28, 2024 (1963).
2. b) I. Kuwajima and T. Mukaiyama, J. Org. Chem., 29, 1385 (1964).
3. c) T. Mukaiyama, R. Matsueda, and M. Suzuki, Tetrahedron Lett., 22, 1901 (1970).
4. d) O. Mitsunobu, Synthesis, 1981, 1.
5. T. Shintou, W. Kikuchi, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 76, 1645 (2003).
6. T. Mukaiyama, T. Shintou, and K. Fukumoto, J. Am. Chem. Soc., 125, 10538 (2003).
7. T. Shintou and T. Mukaiyama, Chem. Lett., 32, 984 (2003).
8. a) H. Loibner and E. Zbiral, Helv. Chim. Acta, 59, 2100 (1976).
9. b) S. Manna and J. R. Falck, Synth. Commun., 15, 663 (1985).
10. c) B. K. Wilk, Synth. Commun., 23, 2481 (1993).
11. d) M. C. Aesa, G. Baán, L. Novák, and C. Szántay, Synth. Commun., 25, 1545 (1995).
12. e) M. C. Aesa, G. Baán, L. Novák, and C. Szántay, Synth. Commun., 25, 2575 (1995).
13. f) M. C. Aesa, G. Baán, L. Novák, and C. Szántay, Synth. Commun., 26, 909 (1996).
14. g) T. Tsunoda, K. Uemoto, C. Nagino, M. Kawamura, H. Kaku, and S. Itô, Tetrahedron Lett., 40, 7355 (1999).
15. a) A. Mizuno, Y. Hamada, and T. Shioiri, Synthesis, 1980, 1007.
16. b) R. Davis, and K. G. Untch, J. Org. Chem., 46, 2985 (1981).
17. N. Iranpoor, H. Firouzabadi, B. Akhlaghinia, and N. Nowrouzi, J. Org. Chem., 69, 2562 (2004).
18. Preparation of various alkoxydiphenylphosphines: See Refs. 2 or 3. The reactions were carried out at 0°C.