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
<A NAME="RF01503SS-1">1 </A>
Liu Y.
Chen X.
Xue M.
Cao R.
Liu L.
Synthesis
2003,
195
<A NAME="RF01503SS-2">2 </A>
When mixing acetone and dimethyl azodicarboxylate
with CaO or Al2 O3 at r.t. or under reflux
condition, no reaction occurred.
<A NAME="RF01503SS-3A">3a </A>
Mukaiyama T.
Atsumi K.
Takeda T.
Chem. Lett.
1976,
597
<A NAME="RF01503SS-3B">3b </A>
Sepulveda-Arques J.
Romero Arbiol E.
Gonzalez
Rosende ME.
Zaballos Garcia ME.
An. Quim.
1992,
88:
253 ; Chem. Abstr. 1992 , 117 , 251282
<A NAME="RF01503SS-4">4 </A>
Bloch JC.
Tetrahedron
1969,
25:
619
<A NAME="RF01503SS-5A">5a </A>
Chia HA.
Kirk BE.
Taylar DR.
J. Chem. Soc., D
1971,
1144
<A NAME="RF01503SS-5B">5b </A>
Lee CB.
Taylar DR.
J. Chem. Soc., Perkin
Trans. 1
1977,
1463
<A NAME="RF01503SS-5C">5c </A>
Hojo M.
Murakami C.
Aihara H.
Tomita K.
Miura K.
Hosomi A.
J. Organomet. Chem.
1995,
499:
155
<A NAME="RF01503SS-6">6 </A>
Kamimura A.
Gunjigake Y.
Mitsudera H.
Yokoyama S.
Tetrahedron Lett.
1998,
39:
7323
<A NAME="RF01503SS-7A">7a </A>
Colonna FP.
Pitacco G.
Valentin E.
Tetrahedron
1971,
27:
5481
<A NAME="RF01503SS-7B">7b </A>
Fatutta S.
Risaliti A.
Russo C.
Valentin E.
Gazz. Chim. Ital.
1972,
102:
1008
<A NAME="RF01503SS-7C">7c </A>
Pitacco G.
Colonna FP.
Russo C.
Valentin E.
Gazz. Chim. Ital.
1975,
105:
1037
<A NAME="RF01503SS-7D">7d </A>
Benedetti F.
Forchiassin M.
Pispisa G.
Nitti P.
Pitacco G.
Russo C.
Valentin E.
Gazz.
Chim. Ital.
1990,
120:
327
<A NAME="RF01503SS-7E">7e </A>
Felluga F.
Nitti P.
Pizzioli A.
Prodan M.
Russo C.
Gazz.
Chim. Ital.
1996,
126:
297
<A NAME="RF01503SS-7F">7f </A>
Felluga F.
Nitti P.
Ruocco E.
Russo C.
Gazz. Chim. Ital.
1997,
127:
387
<A NAME="RF01503SS-8">8 </A>
Mitsunobu O.
Synthesis
1981,
1
<A NAME="RF01503SS-9">9 </A>
Loibner H.
Zbiral E.
Helv. Chim. Acta
1977,
60:
417
<A NAME="RF01503SS-10">10 </A>
Grandi MJD.
Tilley JW.
Tetrahedron
Lett.
1996,
37:
4327
<A NAME="RF01503SS-11">11 </A>
Gthire RD.
Jenkins ID.
Aust. J. Chem.
1982,
35:
767
<A NAME="RF01503SS-12">12 </A>
David C.
Jenkins ID.
Aust. J. Chem.
1992,
45:
47
<A NAME="RF01503SS-13">13 </A> 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
<A NAME="RF01503SS-14">14 </A>
Crystallographic data have been deposited
with the Cambridge Crystallographic Data Centre as supplementary publication
(CCDC 200312).