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3
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0004214539
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Wiley-Interscience: New York
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(c) Olah, G. A. Halonium Ions; Wiley-Interscience: New York, 1975.
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(1975)
Halonium Ions
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Olah, G.A.1
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4
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0000933024
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(d) Nesmeyanov, A. N.; Makarova, L. G.; Tolstaya, T. P. Tetrahedron 1957, 1, 145.
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Tetrahedron
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Nesmeyanov, A.N.1
Makarova, L.G.2
Tolstaya, T.P.3
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7
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-
33845378118
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-
The Stevens rearrangement of alkyl iodonium ylides is known: (a) Olah, G. A.; Doggweiler, H.; Felberg, J. D. J. Am. Chem. Soc. 1985, 107, 4975.
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The Stevens rearrangement of alkyl iodonium ylides is known: (a) Olah, G. A.; Doggweiler, H.; Felberg, J. D. J. Am. Chem. Soc. 1985, 107, 4975.
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-
-
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8
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9644303111
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2R: (b) Gogonas, E. P.; Nyxas, I.; Hadjiarapoglou, L. P. Synlett 2004, 2563.
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2R: (b) Gogonas, E. P.; Nyxas, I.; Hadjiarapoglou, L. P. Synlett 2004, 2563.
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-
-
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9
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33947086188
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Chloronium and bromonium ylides have been made by the thermal decomposition of 3,5-dicyanodiazoimidazole in chlorobenzene or bromobenzene: (c) Sheppard, W. A.; Webster, Q. J. Am. Chem. Soc. 1973, 95, 2695.
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Chloronium and bromonium ylides have been made by the thermal decomposition of 3,5-dicyanodiazoimidazole in chlorobenzene or bromobenzene: (c) Sheppard, W. A.; Webster, Q. J. Am. Chem. Soc. 1973, 95, 2695.
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11
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0001299152
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(b) Hayasi, Y.; Okada, T.; Kawanish, M. Bull. Chem. Soc. Jpn. 1979, 43, 2506.
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Bull. Chem. Soc. Jpn
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Hayasi, Y.1
Okada, T.2
Kawanish, M.3
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16
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22244481889
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The synthetic value of 2-halo-3-alkoxyenones is that they potentially offer a highly functionalized substrate for syntheses using palladium coupling. Compound 4 yields the tricyclic benzofuran system upon intramolecular Heck reaction: Ma, D.; Cai, Q.; Xie, X. Synlett 2005, 11, 1767.
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The synthetic value of 2-halo-3-alkoxyenones is that they potentially offer a highly functionalized substrate for syntheses using palladium coupling. Compound 4 yields the tricyclic benzofuran system upon intramolecular Heck reaction: Ma, D.; Cai, Q.; Xie, X. Synlett 2005, 11, 1767.
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18
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0025827287
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(b) Negishi, E.; Owczarczyk, Z. R.; Swanson, D. R. Tetrahedron Lett. 1991, 32, 4453.
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Tetrahedron Lett
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Negishi, E.1
Owczarczyk, Z.R.2
Swanson, D.R.3
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19
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0025828080
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(c) Rabat, M.; Kiegiel, J.; Cohen, N. K.; Toth, P.; Wovkulich, M.; Uskokovic, M. R. Tetrahedron Lett. 1991, 32, 2343.
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Rabat, M.1
Kiegiel, J.2
Cohen, N.K.3
Toth, P.4
Wovkulich, M.5
Uskokovic, M.R.6
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20
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0026527455
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(d) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919.
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Tetrahedron Lett
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Johnson, C.R.1
Adams, J.P.2
Braun, M.P.3
Senanayake, C.B.W.4
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22
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0027973724
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(f) Johnson, C. R.; Harikrishnan, L. S.; Golebiowski, A. Tetrahedron Lett. 1994, 35, 7735.
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(1994)
Tetrahedron Lett
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Johnson, C.R.1
Harikrishnan, L.S.2
Golebiowski, A.3
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23
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2142785195
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(g) Johnson, C. R.; Adams, J. P.; Collins, M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1.
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J. Chem. Soc., Perkin Trans. 1
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Johnson, C.R.1
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Collins, M.A.3
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24
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45249104772
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-
4b
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4b
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-
-
-
25
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33751155388
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A similar arylation reaction has been observed in the rhodium carboxylate catalyzed reaction of 2-diazo-1,3-cyclohexanedione with fluorobenzene. 2-(4-Fluorophenyl)-1,3-cyclohexanedione was obtained. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem. 1995, 60, 2112.
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A similar arylation reaction has been observed in the rhodium carboxylate catalyzed reaction of 2-diazo-1,3-cyclohexanedione with fluorobenzene. 2-(4-Fluorophenyl)-1,3-cyclohexanedione was obtained. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem. 1995, 60, 2112.
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26
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45249092870
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4 under the standard conditions. Using HRMS, only masses corresponding to 2-chloro-5,5-dimethyl-3- benzyloxycyclohex-2-enone and 2-bromo-5,5-dimethyl-3-(3-methylbenzyloxy) cyclohex-2-enone were detected. No crossover products, 2-chloro-5,5-dimethyl-3- (3-methylbenzyloxy)cyclohex-2-enone and 2-bromo-5,5-dimethyl-3- benzyloxycyclohex-2-enone, were detected.
-
4 under the standard conditions. Using HRMS, only masses corresponding to 2-chloro-5,5-dimethyl-3- benzyloxycyclohex-2-enone and 2-bromo-5,5-dimethyl-3-(3-methylbenzyloxy) cyclohex-2-enone were detected. No crossover products, 2-chloro-5,5-dimethyl-3- (3-methylbenzyloxy)cyclohex-2-enone and 2-bromo-5,5-dimethyl-3- benzyloxycyclohex-2-enone, were detected.
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-
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27
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33947457291
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3/Pyr. Burwell, R. I.; Shields, A. D.; Hart, H. H. J. Am. Chem. Soc. 1954, 76, 908. The starting optical purity determined by chiral gas chromatography was 87% S, 13% R. The yield of 6 was 78.6% S, 21.4% R determined by chiral HPLC. Hydrolysis of 6 was nontrivial. Several standard acid-catalyzed ether cleavage reactions proceeded with benzylic oxygen cleavage. Method 6 to 7 to 8 (Scheme 2) is uniquely suited for the present case and to the best of our knowledge is a novel process.
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3/Pyr. Burwell, R. I.; Shields, A. D.; Hart, H. H. J. Am. Chem. Soc. 1954, 76, 908. The starting optical purity determined by chiral gas chromatography was 87% S, 13% R. The yield of 6 was 78.6% S, 21.4% R determined by chiral HPLC. Hydrolysis of 6 was nontrivial. Several standard acid-catalyzed ether cleavage reactions proceeded with benzylic oxygen cleavage. Method 6 to 7 to 8 (Scheme 2) is uniquely suited for the present case and to the best of our knowledge is a novel process.
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28
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45249093770
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Rhodium was not included in the calculations
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Rhodium was not included in the calculations.
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29
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33750472996
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(a) Bakalbassis, E. G.; Spyroudis, S.; Tsiotra, E. J. Org. Chem. 2006, 71, 7060-7062.
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Spyroudis, S.2
Tsiotra, E.3
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31
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0010451775
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An iodonio-Claisen process has been reported: (a) Ochiai, M.; Ito, T. J. Org. Chem. 1996, 60, 2274-2275.
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An iodonio-Claisen process has been reported: (a) Ochiai, M.; Ito, T. J. Org. Chem. 1996, 60, 2274-2275.
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33
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37049081784
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(c) Ochiai, M.; Ito, T.; Masaki, Y. J. Chem. Soc., Chem. Commun. 1992, 1, 15.
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(d) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y. J. Am. Chem. Soc. 1991, 113, 1319.
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J. Am. Chem. Soc
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35
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33845377543
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(a) Moriarty, R. M.; Bailey, B. R., III; Prakash, O.; Prakash, I. J. Am. Chem. Soc. 1985, 107, 1375.
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J. Am. Chem. Soc
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Moriarty, R.M.1
Bailey III, B.R.2
Prakash, O.3
Prakash, I.4
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37049068193
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(b) Yang, R.-Y.; Dai, L.-X.; Chem, C. G. J. Chem. Soc., Chem. Commun. 1992, 1487.
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Yang, R.-Y.1
Dai, L.-X.2
Chem, C.G.3
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37
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45249102116
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For a discussion of the formation of intermediates analogous to 11 formed from Rh(II) catalytic decomposition of α-diazodicarbonyl compounds, see: (a) Taber, D. F.; Hennessy, M. J.; Hoermer, R. S.; Raman, K.; Ruckle, R. E., Jr.; Schuchardt, J. S. Catalysis of Organic Reactions; Blackburn, D. W., Ed.; Dekker: New York, 1990; Chapter 4, p 43.
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For a discussion of the formation of intermediates analogous to 11 formed from Rh(II) catalytic decomposition of α-diazodicarbonyl compounds, see: (a) Taber, D. F.; Hennessy, M. J.; Hoermer, R. S.; Raman, K.; Ruckle, R. E., Jr.; Schuchardt, J. S. Catalysis of Organic Reactions; Blackburn, D. W., Ed.; Dekker: New York, 1990; Chapter 4, p 43.
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