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Volumn 130, Issue 24, 2008, Pages 7564-7565

The mechanism of 1,4 alkyl group migration in hypervalent halonium ylides: The stereochemical course

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; IODINE DERIVATIVE;

EID: 45249087416     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja802735f     Document Type: Article
Times cited : (41)

References (38)
  • 3
    • 0004214539 scopus 로고
    • Wiley-Interscience: New York
    • (c) Olah, G. A. Halonium Ions; Wiley-Interscience: New York, 1975.
    • (1975) Halonium Ions
    • Olah, G.A.1
  • 7
    • 33845378118 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 8
    • 9644303111 scopus 로고    scopus 로고
    • 2R: (b) Gogonas, E. P.; Nyxas, I.; Hadjiarapoglou, L. P. Synlett 2004, 2563.
    • 2R: (b) Gogonas, E. P.; Nyxas, I.; Hadjiarapoglou, L. P. Synlett 2004, 2563.
  • 9
    • 33947086188 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 16
    • 22244481889 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 24
    • 45249104772 scopus 로고    scopus 로고
    • 4b
    • 4b
  • 25
    • 33751155388 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 26
    • 45249092870 scopus 로고    scopus 로고
    • 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.
  • 27
    • 33947457291 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 28
    • 45249093770 scopus 로고    scopus 로고
    • Rhodium was not included in the calculations
    • Rhodium was not included in the calculations.
  • 31
    • 0010451775 scopus 로고    scopus 로고
    • An iodonio-Claisen process has been reported: (a) Ochiai, M.; Ito, T. J. Org. Chem. 1996, 60, 2274-2275.
    • An iodonio-Claisen process has been reported: (a) Ochiai, M.; Ito, T. J. Org. Chem. 1996, 60, 2274-2275.
  • 37
    • 45249102116 scopus 로고    scopus 로고
    • 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.
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.