The Preparation of Vinylhydrazinedicarboxylates from Ketones via Mitsunobu­ Reaction

Yu-xiu Liu; Cheng-fu Xu; Lun-zu Liu

doi:10.1055/s-2003-40202

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Synthesis 2003(9): 1335-1338
DOI: 10.1055/s-2003-40202

PAPER

The Preparation of Vinylhydrazinedicarboxylates from Ketones via Mitsunobu Reaction

Yu-xiu Liu, Cheng-fu Xu, Lun-zu Liu*
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People’s Republic of China
e-Mail: liu_yuxiu@eyou.com;

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Publikationsverlauf

Received 24 February 2003
Publikationsdatum:
24. Juni 2003 (online)

Abstract
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Abstract

A general method for converting aryl or alkyl methyl ketones to vinylhydrazinedicarboxylates via the Mitsunobu reaction is reported. Unsymmetrical alkyl ketones show high regioselectivity.

Key words

tributylphosphine - triphenylphosphine - dimethyl azodicarboxylate - vinylhydrazinedicarboxylates - Mitsunobu reaction

References

1 Liu Y. Chen X. Xue M. Cao R. Liu L. Synthesis 2003, 195

Artikel in Thieme Connect Google Scholar
3a Mukaiyama T. Atsumi K. Takeda T. Chem. Lett. 1976, 597

Google Scholar
3b Sepulveda-Arques J. Romero Arbiol E. Gonzalez Rosende ME. Zaballos Garcia ME. An. Quim. 1992, 88: 253 ; Chem. Abstr. 1992, 117, 251282

Google Scholar
4 Bloch JC. Tetrahedron 1969, 25: 619

Crossref Google Scholar
5a Chia HA. Kirk BE. Taylar DR. J. Chem. Soc., D 1971, 1144

Crossref Google Scholar
5b Lee CB. Taylar DR. J. Chem. Soc., Perkin Trans. 1 1977, 1463

Crossref Google Scholar
5c Hojo M. Murakami C. Aihara H. Tomita K. Miura K. Hosomi A. J. Organomet. Chem. 1995, 499: 155

Crossref Google Scholar
6 Kamimura A. Gunjigake Y. Mitsudera H. Yokoyama S. Tetrahedron Lett. 1998, 39: 7323

Crossref Google Scholar
7a Colonna FP. Pitacco G. Valentin E. Tetrahedron 1971, 27: 5481

Google Scholar
7b Fatutta S. Risaliti A. Russo C. Valentin E. Gazz. Chim. Ital. 1972, 102: 1008

Google Scholar
7c Pitacco G. Colonna FP. Russo C. Valentin E. Gazz. Chim. Ital. 1975, 105: 1037

Google Scholar
7d Benedetti F. Forchiassin M. Pispisa G. Nitti P. Pitacco G. Russo C. Valentin E. Gazz. Chim. Ital. 1990, 120: 327

Google Scholar
7e Felluga F. Nitti P. Pizzioli A. Prodan M. Russo C. Gazz. Chim. Ital. 1996, 126: 297

Google Scholar
7f Felluga F. Nitti P. Ruocco E. Russo C. Gazz. Chim. Ital. 1997, 127: 387

Google Scholar
8 Mitsunobu O. Synthesis 1981, 1

Artikel in Thieme Connect Google Scholar
9 Loibner H. Zbiral E. Helv. Chim. Acta 1977, 60: 417

Crossref Google Scholar
10 Grandi MJD. Tilley JW. Tetrahedron Lett. 1996, 37: 4327

Google Scholar
11 Gthire RD. Jenkins ID. Aust. J. Chem. 1982, 35: 767

Crossref Google Scholar
12 David C. Jenkins ID. Aust. J. Chem. 1992, 45: 47

Google Scholar
13 For the theory of β-elimination, including mechanism, orientation effects and stereochemistry, see: Carey FA. Sundberg RJ. Advanced Organic Chemistry Plenum; New York: 1977. 2nd ed. Part A. p.345-361

Google Scholar

2

When mixing acetone and dimethyl azodicarboxylate with CaO or Al₂O₃ at r.t. or under reflux condition, no reaction occurred.

14

Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication (CCDC 200312).