메뉴 건너뛰기




Volumn , Issue 7, 1999, Pages 1085-1087

Generation and reactions of ammonium ylides in basic two-phase systems: Convenient synthesis of cyclopropanes, oxiranes and alkenes substituted with electron-withdrawing groups

Author keywords

Alkenes; Ammonium ylides; Cyclopropanes; Oxiranes; Quaternary ammonium salts

Indexed keywords

ALDEHYDE; ALKENE; ALKYLATING AGENT; CARBONIC ACID DERIVATIVE; CYCLOPROPANE; DICHLOROMETHANE; ETHYLENE OXIDE; QUATERNARY AMMONIUM DERIVATIVE; SODIUM HYDROXIDE;

EID: 0242435030     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2757     Document Type: Article
Times cited : (35)

References (32)
  • 1
    • 0003487195 scopus 로고
    • Editura Academiei Republicii Socialiste Romãnia, Bucuresti and Mc Graw-Hill, New York
    • Zugrǎvescu, I.; Petrovanu, M. N-Ylid Chemistry; Editura Academiei Republicii Socialiste Romãnia, Bucuresti and Mc Graw-Hill, New York, 1976.
    • (1976) N-Ylid Chemistry
    • Zugrǎvescu, I.1    Petrovanu, M.2
  • 3
    • 0000102616 scopus 로고
    • Pine, S. H. Org. React. 1970, 18, 403. Maeda, Y.; Shirai, N.; Sato, Y. J. Chem. Soc., Perkin Trans. I 1994, 393 and the references cited therein. Zdrojewski, T.; Jończyk, A. J. Org. Chem. 1998, 63, 452 and the references cited therein.
    • (1970) Org. React. , vol.18 , pp. 403
    • Pine, S.H.1
  • 4
    • 37049089613 scopus 로고
    • Pine, S. H. Org. React. 1970, 18, 403. Maeda, Y.; Shirai, N.; Sato, Y. J. Chem. Soc., Perkin Trans. I 1994, 393 and the references cited therein. Zdrojewski, T.; Jończyk, A. J. Org. Chem. 1998, 63, 452 and the references cited therein.
    • (1994) J. Chem. Soc., Perkin Trans. I , pp. 393
    • Maeda, Y.1    Shirai, N.2    Sato, Y.3
  • 5
    • 0009118055 scopus 로고    scopus 로고
    • and the references cited therein
    • Pine, S. H. Org. React. 1970, 18, 403. Maeda, Y.; Shirai, N.; Sato, Y. J. Chem. Soc., Perkin Trans. I 1994, 393 and the references cited therein. Zdrojewski, T.; Jończyk, A. J. Org. Chem. 1998, 63, 452 and the references cited therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 452
    • Zdrojewski, T.1    Jończyk, A.2
  • 9
    • 0000002236 scopus 로고
    • Padwa, A., Ed.; John Wiley & Sons; New York
    • Cycloaddition of azomethine ylides: Lown, J. W. in 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed.; John Wiley & Sons; New York, 1984, Vol. 1, p. 653.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.1 , pp. 653
    • Lown, J.W.1
  • 10
    • 0344070946 scopus 로고    scopus 로고
    • note
    • 4S: C, 45.44; H, 7.63; N, 10.60. Found: C, 45.49; H, 7.63; N, 10.57.
  • 13
    • 0000555112 scopus 로고
    • 11 (PTC) reactions of arylacetonitriles with carbon tetrachloride and electrophilic alkenes or aromatic aldehydes, respectively: Makosza, M.; Kwast, A.; Kwast, E.; Jończyk, A. J. Org. Chem. 1985, 50, 3722. However, their scope is somewhat restricted, side reactions often accompany the main pathway, and the products are formed usually in 40-60% yields.
    • (1985) J. Org. Chem. , vol.50 , pp. 3722
    • Makosza, M.1    Kwast, A.2    Kwast, E.3    Jończyk, A.4
  • 14
    • 0003443131 scopus 로고
    • Verlag Chemie, Weinheim
    • Dehmlow, E, V.; Dehmlow, S. S. Phase Transfer Catalysis; 3rd Ed.; Verlag Chemie, Weinheim, 1993. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-transfer Catalysis; Chapman & Hall; New York, London, 1994. Ma+ (Combining ogonek)kosza, M.; Fedoryński, M. Polish J. Chem. 1996, 70, 1093. Ma+ (Combinig ogonek)kosza, M.; Fedoryński, M, in Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional; London, 1997, p. 135.
    • (1993) Phase Transfer Catalysis; 3rd Ed.
    • Dehmlow, E.V.1    Dehmlow, S.S.2
  • 15
    • 0003533112 scopus 로고
    • Chapman & Hall; New York, London
    • Dehmlow, E, V.; Dehmlow, S. S. Phase Transfer Catalysis; 3rd Ed.; Verlag Chemie, Weinheim, 1993. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-transfer Catalysis; Chapman & Hall; New York, London, 1994. Ma+ (Combining ogonek)kosza, M.; Fedoryński, M. Polish J. Chem. 1996, 70, 1093. Ma+ (Combining ogonek)kosza, M.; Fedoryński, M, in Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional; London, 1997, p. 135.
    • (1994) Phase-transfer Catalysis
    • Starks, C.M.1    Liotta, C.L.2    Halpern, M.3
  • 16
    • 0030515785 scopus 로고    scopus 로고
    • Dehmlow, E, V.; Dehmlow, S. S. Phase Transfer Catalysis; 3rd Ed.; Verlag Chemie, Weinheim, 1993. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-transfer Catalysis; Chapman & Hall; New York, London, 1994. Ma+ (Combining ogonek)kosza, M.; Fedoryński, M. Polish J. Chem. 1996, 70, 1093. Ma+ (Combining ogonek)kosza, M.; Fedoryński, M, in Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional; London, 1997, p. 135.
    • (1996) Polish J. Chem. , vol.70 , pp. 1093
    • Makosza, M.1    Fedoryński, M.2
  • 17
    • 0001866366 scopus 로고    scopus 로고
    • Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional; London
    • Dehmlow, E, V.; Dehmlow, S. S. Phase Transfer Catalysis; 3rd Ed.; Verlag Chemie, Weinheim, 1993. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-transfer Catalysis; Chapman & Hall; New York, London, 1994. Ma+ (Combining ogonek)kosza, M.; Fedoryński, M. Polish J. Chem. 1996, 70, 1093. Ma+ (Combining ogonek)kosza, M.; Fedoryński, M, in Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional; London, 1997, p. 135.
    • (1997) Handbook of Phase Transfer Catalysis , pp. 135
    • Makosza, M.1    Fedoryński, M.2
  • 19
    • 0344070942 scopus 로고    scopus 로고
    • note
    • For example, reaction of salt la with an excess of methacrylonitrile under conditions A, gives 1,2-dicyano-1-methyl-2-phenylcyclopropane, in 27% yield.
  • 20
    • 0344502104 scopus 로고    scopus 로고
    • note
    • Irradiation of signals of oxirane protons at δ = 4.10 ppm or δ = 4.51 ppm in Z and E isomers mixture of 6ca resulted in increase of only one signal of olefinic protons at δ = 5.40 -5.45 ppm (m), namely from Z-isomer.
  • 21
    • 0000746196 scopus 로고
    • Syntheses of oxirane substituted with EWG: Ballester, M. Chem. Rev. 1955, 55, 283, Newman, M. S.; Magerlein, B. J. Org. React. 1957, 5, 413. Shibata, I.; Yamasaki, H.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909 and the references cited therein.
    • (1955) Chem. Rev. , vol.55 , pp. 283
    • Ballester, M.1
  • 22
    • 0001400335 scopus 로고
    • Syntheses of oxirane substituted with EWG: Ballester, M. Chem. Rev. 1955, 55, 283, Newman, M. S.; Magerlein, B. J. Org. React. 1957, 5, 413. Shibata, I.; Yamasaki, H.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909 and the references cited therein.
    • (1957) Org. React. , vol.5 , pp. 413
    • Newman, M.S.1    Magerlein, B.J.2
  • 23
    • 0001457852 scopus 로고
    • and the references cited therein
    • Syntheses of oxirane substituted with EWG: Ballester, M. Chem. Rev. 1955, 55, 283, Newman, M. S.; Magerlein, B. J. Org. React. 1957, 5, 413. Shibata, I.; Yamasaki, H.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 6909 and the references cited therein.
    • (1992) J. Org. Chem. , vol.57 , pp. 6909
    • Shibata, I.1    Yamasaki, H.2    Baba, A.3    Matsuda, H.4
  • 25
    • 0344070941 scopus 로고    scopus 로고
    • note
    • +- may generate cyano-2-thicnyl carbene which after dimerization produces 8. However, our attempts to intercept this carbene with n-butylvinyl ether, failed.
  • 27
    • 0344070940 scopus 로고
    • Ma+ (Combining ogonek)kosza, M.; Serafinowa, B.; Gajos, I. Roczniki Chem. 1969, 43, 671; Chem. Abstr. 1969, 71, 101 498.
    • (1969) Chem. Abstr. , vol.71 , Issue.101 , pp. 498
  • 32
    • 0344070918 scopus 로고    scopus 로고
    • note
    • 2 (20 mL) was vigorously stirred, bromide 4d (0.86 g, 5 mmol) then 50% aq NaOH (7 mL) were added (exothermal effect), reaction was continued for 4h, and worked up as described for 5ac. The product was purified by Kugelrohr distillation [bp 125-130 °C (oven)/0.03 Torr] to give 0.81 g (89%) of oily 7cd (Table 3, Entry 6).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.