Abstract
An improved procedure for preparing the title compound, resulting in substantially
higher yields under simpler conditions, is described.
Key words
phase-transfer catalysis - cycloadditions - photochemistry - cuprates - carbenes
References
<A NAME="RM00107SS-1A">1a </A>
Zollinger H.
Diazo Chemistry
Vol. 2:
VCH Publishers;
Weinheim:
1995.
<A NAME="RM00107SS-1B">1b </A>
Regitz M.
Maas G.
Diazo Compounds. Properties and Syntheses
Academic Press;
Orlando:
1986.
<A NAME="RM00107SS-2">2 </A>
Chemistry of Diazirines
Liu MTH.
CRC Press;
Boca Raton:
1987.
<A NAME="RM00107SS-3A">3a </A>
Moss RA.
Advances in Carbene Chemistry
Vol. 3:
Brinker UH.
Elsevier;
Amsterdam:
2001.
p.53
<A NAME="RM00107SS-3B">3b </A>
Toscano JP.
Wang Y.
J. Am. Chem. Soc.
2000,
122:
4512
<A NAME="RM00107SS-3C">3c </A>
Motschiedler K.
Gudmundsdottir A.
Toscano JP.
Platz M.
Garcia-Garibay MA.
J. Org. Chem.
1999,
64:
5139
<A NAME="RM00107SS-3D">3d </A>
Bonneau R.
Liu MTH.
Advances in Carbene Chemistry
Vol. 2:
Brinker UH.
JAI Press;
Stamford USA:
1998.
p.1
<A NAME="RM00107SS-3E">3e </A>
Ford F.
Yuzawa T.
Platz MS.
Matzinger S.
Fuelscher M.
J. Am. Chem. Soc.
1998,
120:
4430
<A NAME="RM00107SS-3F">3f </A>
Huang H.
Platz MS.
J. Am. Chem. Soc.
1998,
120:
5990
<A NAME="RM00107SS-3G">3g </A>
Platz MS.
Advances in Carbene Chemistry
Vol. 2:
Brinker UH.
JAI Press;
Stamford USA:
1998.
p.133
<A NAME="RM00107SS-3H">3h </A>
Pezacki JP.
Pole DL.
Warkentin J.
Chen T.
Ford F.
Toscano J.
Fell J.
Platz MS.
J. Am. Chem. Soc.
1997,
119:
3191
<A NAME="RM00107SS-3I">3i </A>
Huang H.
Platz MS.
Tetrahedron Lett.
1996,
37:
8337
<A NAME="RM00107SS-3J">3j </A>
Yamamoto N.
Bernardi F.
Bottoni A.
Olivucci M.
Robb MA.
Wilsey S.
J. Am. Chem. Soc.
1994,
116:
2064
<A NAME="RM00107SS-3K">3k </A>
Celebi S.
Leyva S.
Modarelli DA.
Platz MS.
J. Am. Chem. Soc.
1993,
115:
8613
<A NAME="RM00107SS-3L">3l </A>
Fox JM.
Scacheri JEG.
Jones KGL.
Jones M.
Shevlin PB.
Armstrong B.
Sztyrbicka R.
Tetrahedron Lett.
1992,
33:
5021
<A NAME="RM00107SS-3M">3m </A>
Modarelli DA.
Morgan S.
Platz MS.
J. Am. Chem. Soc.
1992,
114:
7034
<A NAME="RM00107SS-3N">3n </A>
Seburg RA.
McMahon RJ.
J. Am. Chem. Soc.
1992,
114:
7183
<A NAME="RM00107SS-3O">3o </A>
White WR.
Platz MS.
J. Org. Chem.
1992,
57:
2841
<A NAME="RM00107SS-3P">3p </A>
Tomioka H.
Kitagawa H.
Izawa Y.
J. Org. Chem.
1979,
44:
3072
<A NAME="RM00107SS-4">4 </A>
Shevlin PB. In Reactive Intermediate Chemistry
Moss RA.
Platz MS.
Jones M.
Wiley;
New York:
2004.
p.463
<A NAME="RM00107SS-5A">5a </A>
Farlow RA.
Thamattoor DM.
Sunoj RB.
Hadad CM.
J. Org. Chem.
2002,
67:
3257
<A NAME="RM00107SS-5B">5b </A>
Thamattoor DM.
Snoonian JR.
Sulzbach HM.
Hadad CM.
J. Org. Chem.
1999,
64:
5886
<A NAME="RM00107SS-5C">5c </A>
Nigam M.
Platz MS.
Showalter BM.
Toscano JP.
Johnson R.
Abbot SC.
Kirchhoff MM.
J. Am. Chem. Soc.
1998,
120:
8055
<A NAME="RM00107SS-5D">5d </A>
Robert M.
Likhotvorik I.
Platz MS.
Abbot SC.
Kirchoff MM.
Johnson R.
J. Phys. Chem. A
1998,
102:
1507
<A NAME="RM00107SS-5E">5e </A>
Ruck RT.
Jones M.
Tetrahedron Lett.
1998,
39:
2277
<A NAME="RM00107SS-5F">5f </A>
Ruck RT.
Jones M.
Tetrahedron Lett.
1998,
39:
4433
<A NAME="RM00107SS-5G">5g </A>
Glick HC.
Likhovorik IR.
Jones M.
Tetrahedron Lett.
1995,
36:
5715
<A NAME="RM00107SS-5H">5h </A>
Chateauneuf JE.
Johnson RP.
Kirchhoff MM.
J. Am. Chem. Soc.
1990,
112:
3217
<A NAME="RM00107SS-5I">5i </A>
Richardson DB.
Durrett LR.
Martin JM.
Putnam WE.
Slaymaker SC.
Dvoretzky I.
J. Am. Chem. Soc.
1965,
87:
2763
<A NAME="RM00107SS-6A">6a </A>
Kitatani K.
Hiyama T.
Nozaki H.
J. Am. Chem. Soc.
1976,
98:
2362
<A NAME="RM00107SS-6B">6b </A>
Kitatani K.
Hiyama T.
Nozaki H.
Bull. Chem. Soc. Jpn.
1977,
50:
1600
<A NAME="RM00107SS-7">7 </A>
Schäffler J.
Deppisch B.
Rétey J.
Chem. Ber.
1982,
115:
2229
<A NAME="RM00107SS-8">8 </A>
Joshi GC.
Singh N.
Pande LM.
Synthesis
1972,
317
<A NAME="RM00107SS-9">9 </A>
Initially, we stopped the reaction too soon. For optimal results, the reaction time
was extended as indicated. Since the product is only partially soluble in CH2 Cl2 , we originally removed all the solvent from the suspension using a rotary evaporator.
This, however, led to an intractable, dark semi-solid from which the product was difficult
to isolate. Filtration of the product, prior to solvent removal and work-up, instead
led to substantially improved yields.
<A NAME="RM00107SS-10">10 </A>
Dehmlow EV.
Wilkenloh J.
J. Chem. Res., Synop.
1984,
396
<A NAME="RM00107SS-11">11 </A> See also:
Preda DV.
Scott LT.
Tetrahedron Lett.
2000,
41:
9633 ; and references cited therein