4076
H. Matsubara et al. / Tetrahedron 58ꢀ2002) 4071±4076
equipped with an inserted glass linerꢀ The autoclave was
pressurized with 80 atm of CO and stirred for 3 h at
1998, 31, 641±650ꢀ .b) Curran, Dꢀ Pꢀ Angew. Chem. Int. Ed.
Engl. 1998, 37, 1174±1196ꢀ .c) Cornils, Bꢀ Angew. Chem. Int.
Ed. Engl. 1997, 36, 2057±2059ꢀ .d) Barthel-Rosa, Lꢀ Pꢀ;
Gladysz, Jꢀ Aꢀ Coord. Chem. Rev. 1999, 192, 587±605ꢀ .e)
Luo, Zꢀ; Zhang, Qꢀ; Oderaotoshi, Yꢀ; Curran, Dꢀ Pꢀ Science
2001, 291, 1766±1769ꢀ
9
08Cꢀ After cooling, the mixture was diluted with CH Cl
2 2
.
FC-72ꢀ The CH Cl layer was dried over MgSO4 and
20 mL), washed twice with H O and three times with
2
2
2
concentrated in vacuoꢀ The residue was puri®ed by column
chromatography on silica gel .B 8 mm£40 mm) with
hexane/ethyl acetate .2:1) to afford 1-adamantylmethanol
2ꢀ For some recent reports, see .a) Ryu, Iꢀ; Sergio, Kꢀ; Niguma,
Tꢀ; Minakata, Sꢀ; Komatsu, Mꢀ; Luo, Zꢀ; Curran, Dꢀ Pꢀ
Tetrahedron Lett. 2001, 42, 947±950ꢀ .b) Soos, Tꢀ; Bennett,
Bꢀ Lꢀ; Rutherford, Dꢀ; Barthel-Rosa, Lꢀ Pꢀ; Gladysz, Jꢀ Aꢀ
Organometallics 2001, 20, 3079±3086ꢀ .c) Rocaboy, Cꢀ;
Rutherford, Dꢀ; Bennett, Bꢀ Lꢀ; Gladysz, Jꢀ Aꢀ J. Phys. Org.
Chem. 2000, 13, 596±603ꢀ .d) Falck, Jꢀ Rꢀ; Yu, Jꢀ; Cho, Hꢀ-Sꢀ
Tetrahedron Lett. 1994, 35, 5997±6000ꢀ .e) Nakamura, Hꢀ;
Linclau, Bꢀ; Curran, Dꢀ Pꢀ J. Am. Chem. Soc. 2001, 123,
10119±10120ꢀ .f) Crich, Dꢀ; Neelamkavil, Sꢀ J. Am. Chem.
Soc. 2001, 123, 7449±7450ꢀ .g) Rocaboy, Cꢀ; Bauer, Wꢀ;
Gladysz, Jꢀ Aꢀ Eur. J. Chem. 2000, 2621±2628ꢀ .h) Zhang,
Qꢀ; Luo, Zꢀ; Curran, Dꢀ Pꢀ J. Org. Chem. 2000, 65, 8866±8873ꢀ
3ꢀ Ogawa, Aꢀ; Curran, Dꢀ Pꢀ J. Org. Chem. 1997, 62, 450±451ꢀ
4ꢀ .a) Curran, Dꢀ Pꢀ In Stimulating Concepts in Chemistry,
Stoddard, Fꢀ, Reinhoudt, Dꢀ, Shibasaki, Mꢀ, Edsꢀ; Wiley±
VCH: New York, 2000; pꢀ 25ꢀ .b) Kitazume, Tꢀ J. Flourine
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.142 mg, 85%)ꢀ The second run which reused the F-626
solution of 3 gave 133 mg .80%) of the productꢀ
4.1.7. Typical procedure for the Vilsmeier formylation.
Phosphorus oxychloride .1ꢀ3 mmol) was added to a mixture
of aromatic compound .1 mmol), N-methylformanilide .1ꢀ
3 mmol) in F-626 .1 mL)ꢀ The reaction mixture was heated
at 1008C for 1 hꢀ After cooling, the upper layer was
decanted, and the residue was diluted with benzene
10 mL), washed with twice of H O and three times of
2
.
FC-72ꢀ The solution was dried over MgSO , and concen-
4
trated in vacuoꢀ The residue was puri®ed by column
chromatography on silica gel .B 8 mm£40 mm) with
benzene to give the formylation productꢀ When o-dichloro-
benzne was used as a solvent, the same procedure was
carried out without decantation and washing the benzene
solution with FC-72ꢀ
5
ꢀ .a) Fujii, Yꢀ; Tamura, Eꢀ; Yano, Sꢀ; Furugaki, Hꢀ US Patent
6,060,626; 2000 .b) Fujii, Yꢀ; Furugaki, Hꢀ; Yano, Sꢀ; Kita, Kꢀ
Chem. Lett. 2000, 926±927ꢀ
4
.1.8. Typical procedure for the Wolff±Kishner reduc-
tion. To a mixture of carbonyl compound .2ꢀ5 mmol) and
powder of potassium hydroxide .5 mmol) in F-626 .2 mL),
hydrazine monohydrate .1 mL) was added and heated at
6ꢀ Curran, Dꢀ Pꢀ; Hadida, Sꢀ; Kim, Sꢀ-Yꢀ; Luo, Zꢀ J. Am. Chem.
Soc. 1999, 121, 6607±6615ꢀ
1208C for 2 hꢀ The reaction mixture was re¯uxed for 6 hꢀ
After cooling, the reaction mixture was diluted with
7ꢀ Curran, Dꢀ Pꢀ; Hadida, Sꢀ J. Am. Chem. Soc. 1996, 118, 2531±
2532ꢀ
benzene .10 mL), washed with twice of H O and three
2
times of FC-72ꢀ The solution was dried over MgSO and
4
8ꢀ .a) Ryu, Iꢀ; Niguma, Tꢀ; Minakata, Sꢀ; Komatsu, Mꢀ; Curran,
Dꢀ Pꢀ; Hadida, Sꢀ Tetrahedron Lett. 1997, 38, 7883±7886ꢀ
.b) Ryu, Iꢀ; Niguma, Tꢀ; Minakata, Sꢀ; Komatsu, Mꢀ; Luo,
Zꢀ; Curran, Dꢀ Pꢀ Tetrahedron Lett. 1999, 40, 2367±2370ꢀ
For reviews on radical carbonylations and acyl radicals, see:
.c) Ryu, Iꢀ Chem. Soc. Rev. 2001, 30, 16±25ꢀ .d) Chatgilialoglu,
Cꢀ; Crich, Dꢀ; Komatsu, Mꢀ; Ryu, Iꢀ Chem. Rev. 1999, 99,
concentrated in vacuoꢀ The residue was puri®ed by column
chromatography on silica gel .B 8 mm£40 mm) with
benzene to give the reduction productꢀ When diethylene
glycol was used as a solvent, the same treatment was
undertaken without washing with FC-72ꢀ
1
991±2068ꢀ .e) Ryu, Iꢀ; Sonoda, Nꢀ; Curran, Dꢀ Pꢀ Chem.
4
.1.9. Typical procedure for the Diels±Alder reaction.
An equimolar mixture of diene .1ꢀ3 mmol) and dienophile
1ꢀ3 mmol) in solvent .3 mL) was re¯uxed until the red
Rev. 1996, 96, 177±194ꢀ .f) Ryu, Iꢀ; Sonoda, Nꢀ Angew.
Chem. Int. Ed. Engl. 1996, 35, 1050±1066ꢀ
ꢀ .a) Vilsmeier, Aꢀ; Haack, Aꢀ Chem. Ber. 1927, 60, 119±122ꢀ
.
9
color of the solution disappeared .about 10 min)ꢀ The sepa-
rated crystals were collected by ®ltration, washed with
benzene .30 mL), and dried in vacuoꢀ Dimethyl 3,4,5,6-
tetraphenylphthlate: white needles, mp 258±2608C .litꢀ
256±2578C) ; 3,4,5,6-tetraphenyl-1,2-dihydro-o-phthalic
11c
anhydride: white needles, mp 252±2548C .litꢀ 2558C)ꢀ
.
b) Olar, Gꢀ Aꢀ; Kuhn, Sꢀ Jꢀ Friedel Crafts and Related
Reactions, Volꢀ 3; Wiley: New York, 1964 Part 2, p 1211ꢀ
c) Seshadri, Sꢀ J. Sci. Ind. Res. 1973, 32, 128ꢀ .d) Fieser,
.
Lꢀ Fꢀ; Hartwell, Jꢀ Lꢀ; Jones, Jꢀ Eꢀ Organic Syntheses, Collectꢀ
Volꢀ III; Wiley: New York, 1955 pp 98±100ꢀ
1
2
1
1
0ꢀ .a) Todd, Tꢀ Org. React. 1948, 4, 378±422ꢀ .b) Minlon, Hꢀ
J. Am. Chem. Soc. 1946, 68, 2487±2488ꢀ
1ꢀ .a) Oppolzer, Wꢀ Comprehensive Organic Synthesis; Trost,
Bꢀ Mꢀ, Fleming, Iꢀ, Edsꢀ; Pergamon: Oxford, 1991; Volꢀ 9,
ppꢀ 315±399ꢀ .b) Holmes, Hꢀ Lꢀ Org. React. 1948, 4, 60±
Acknowledgements
We thank Professor John Mꢀ Murphy for useful suggestions
on the manuscriptꢀ
1
1
73ꢀ .c) Allen, Cꢀ Fꢀ Hꢀ; Sheps, Lꢀ Jꢀ Can. J. Res. 1934, 11,
71±179ꢀ
1
2ꢀ Wakatsuki, Yꢀ; Kuramitsu, Tꢀ; Yamazaki, Hꢀ Tetrahedron
Lett. 1974, 4549±4552ꢀ
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