메뉴 건너뛰기




Volumn 3, Issue 3, 2004, Pages 311-316

Synthesis of cycloalkynes via photochemical decarboxylation of ω-phthalimidoalkynoates

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE DERIVATIVE; CARBON DIOXIDE; HYDROGEN; MACROCYCLIC COMPOUND; PHTHALIMIDE DERIVATIVE;

EID: 3042641846     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b312263h     Document Type: Article
Times cited : (11)

References (44)
  • 1
    • 0003013811 scopus 로고    scopus 로고
    • Laser flash photolysis study of N-alkyl phthalimides
    • A. G. Griesbeck H. Görner Laser flash photolysis study of N-alkyl phthalimides J. Photochem. Photobiol., A 1999 129 111-119.
    • (1999) J. Photochem. Photobiol., A , vol.129 , pp. 111-119
    • Griesbeck, A.G.1    Görner, H.2
  • 3
    • 50849148015 scopus 로고
    • Solvent induced changes in the photophysical properties of N-alkylphthalimides
    • P. B. Filho V. G. Toscano M. J. Politi Solvent induced changes in the photophysical properties of N-alkylphthalimides J. Photochem. Photobiol., A. 1988 43 51-58.
    • (1988) J. Photochem. Photobiol., A. , vol.43 , pp. 51-58
    • Filho, P.B.1    Toscano, V.G.2    Politi, M.J.3
  • 6
    • 33947291863 scopus 로고
    • Cathodic reduction of phthalimide systems in nonaqueous solutions
    • D. W. Leedy D. L. Muck Cathodic reduction of phthalimide systems in nonaqueous solutions J. Am. Chem. Soc. 1971 93 4264-4270.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 4264-4270
    • Leedy, D.W.1    Muck, D.L.2
  • 7
    • 0003071483 scopus 로고
    • Electrochemical reduction mechanism of phthalimide and some of its N-derivatives in DMF
    • G. Farnia A. Romanin G. Capobianco F. Torzo Electrochemical reduction mechanism of phthalimide and some of its N-derivatives in DMF J. Electroanal. Chem. 1971 33 31-44.
    • (1971) J. Electroanal. Chem. , vol.33 , pp. 31-44
    • Farnia, G.1    Romanin, A.2    Capobianco, G.3    Torzo, F.4
  • 8
    • 0242628786 scopus 로고    scopus 로고
    • Photoinduced electron transfer chemistry of phthalimides: An efficient tool for C–C bond formation
    • For reviews, see
    • For reviews, see: M. Oelgemöller A. G. Griesbeck Photoinduced electron transfer chemistry of phthalimides: an efficient tool for C–C bond formation J. Photochem. Photobiol., C 2002 3 109-127.
    • (2002) J. Photochem. Photobiol., C , vol.3 , pp. 109-127
    • Oelgemöller, M.1    Griesbeck, A.G.2
  • 9
    • 0344501416 scopus 로고
    • Electron transfer processes in phthalimide systems
    • W. M. Horspool and P.-S. Song, CRC Press, Boca Raton
    • A. G. Griesbeck and H. Mauder, Electron transfer processes in phthalimide systems, in CRC Handbook of Organic Photochemistry and Photobiology, ed. W. M. Horspool and P.-S. Song, CRC Press, Boca Raton, 1995, pp. 513–521.
    • (1995) CRC Handbook of Organic Photochemistry and Photobiology , pp. 513-521
    • Griesbeck, A.G.1    Mauder, H.2
  • 10
    • 0001751112 scopus 로고
    • The photochemistry of imides
    • A. Padwa, Marcel Dekker, New York
    • P. H. Mazzocchi, The photochemistry of imides, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1981, vol. 5, pp. 421–471.
    • (1981) Organic Photochemistry , vol.5 , pp. 421-471
    • Mazzocchi, P.H.1
  • 11
    • 0002123059 scopus 로고
    • Phthalimide and its derivatives
    • W. M. Horspool, Plenum Press, New York
    • J. D. Coyle, Phthalimide and its derivatives, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum Press, New York, 1984, pp. 259–284.
    • (1984) Synthetic Organic Photochemistry , pp. 259-284
    • Coyle, J.D.1
  • 12
    • 33947093639 scopus 로고
    • Photoreactions of cyclic imides. Examples of synthetic organic photochemistry
    • Y. Kanaoka Photoreactions of cyclic imides. Examples of synthetic organic photochemistry Acc. Chem. Res. 1978 11 407-413.
    • (1978) Acc. Chem. Res. , vol.11 , pp. 407-413
    • Kanaoka, Y.1
  • 13
    • 0032814028 scopus 로고    scopus 로고
    • Synthetic applications of photoinduced electron transfer decarboxylation reactions
    • A. G. Griesbeck W. Kramer M. Oelgemöller Synthetic applications of photoinduced electron transfer decarboxylation reactions Synlett 1999 1169-1178.
    • (1999) Synlett , pp. 1169-1178
    • Griesbeck, A.G.1    Kramer, W.2    Oelgemöller, M.3
  • 16
    • 0036964206 scopus 로고    scopus 로고
    • Synthesis of cyclic peptides by photochemical decarboxylation of N-phthaloyl peptides in aqueous solution
    • A. G. Griesbeck T. Heinrich M. Oelgemöller A. Molis A. Heidtmann Synthesis of cyclic peptides by photochemical decarboxylation of N-phthaloyl peptides in aqueous solution Helv. Chim. Acta 2002 85 4561-4578.
    • (2002) Helv. Chim. Acta , vol.85 , pp. 4561-4578
    • Griesbeck, A.G.1    Heinrich, T.2    Oelgemöller, M.3    Molis, A.4    Heidtmann, A.5
  • 17
    • 0037130633 scopus 로고    scopus 로고
    • A photochemical route for efficient cyclopeptide formation with a minimum of protection and activation chemistry
    • A. G. Griesbeck T. Heinrich M. Oelgemöller J. Lex A. Molis A photochemical route for efficient cyclopeptide formation with a minimum of protection and activation chemistry J. Am. Chem. Soc. 2002 124 10972-10973.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10972-10973
    • Griesbeck, A.G.1    Heinrich, T.2    Oelgemöller, M.3    Lex, J.4    Molis, A.5
  • 18
    • 0032997444 scopus 로고    scopus 로고
    • Decarboxylative photocyclization: Synthesis of benzopyrrolizidines and macrocyclic lactons
    • A. G. Griesbeck F. Nerowski J. Lex Decarboxylative photocyclization: synthesis of benzopyrrolizidines and macrocyclic lactons J. Org. Chem. 1999 64 5213-5217.
    • (1999) J. Org. Chem. , vol.64 , pp. 5213-5217
    • Griesbeck, A.G.1    Nerowski, F.2    Lex, J.3
  • 19
    • 0034731550 scopus 로고    scopus 로고
    • Photochemistry of MTM- and MTE-esters of ω-phthalimido carboxylic acids: Macrocyclization versus deprotection
    • A. G. Griesbeck M. Oelgemöller J. Lex Photochemistry of MTM- and MTE-esters of ω-phthalimido carboxylic acids: macrocyclization versus deprotection J. Org. Chem. 2000 65 9028-9032.
    • (2000) J. Org. Chem. , vol.65 , pp. 9028-9032
    • Griesbeck, A.G.1    Oelgemöller, M.2    Lex, J.3
  • 20
    • 0029088989 scopus 로고
    • An effective synthesis of large ring acetylenes
    • J. Boivin S. Huppé S. Z. Zard An effective synthesis of large ring acetylenes Tetrahedron Lett. 1995 36 5737-5740.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5737-5740
    • Boivin, J.1    Huppé, S.2    Zard, S.Z.3
  • 21
    • 0001521342 scopus 로고
    • Cyclic alkynes, enynes and dienynes. A synthetic challenge
    • For reviews, see
    • For reviews, see H. Meier Cyclic alkynes, enynes and dienynes. A synthetic challenge Adv. Strain Org. Chem. 1991 1 215-272.
    • (1991) Adv. Strain Org. Chem. , vol.1 , pp. 215-272
    • Meier, H.1
  • 22
    • 0001423135 scopus 로고
    • Angle strained cycloalkynes
    • A. Krebs J. Wilke Angle strained cycloalkynes Top. Curr. Chem. 1983 109 189-233.
    • (1983) Top. Curr. Chem. , vol.109 , pp. 189-233
    • Krebs, A.1    Wilke, J.2
  • 24
    • 0001046454 scopus 로고
    • Synthesewege zu Cycloalkinen mittlerer Ringgröße
    • H. Meier Synthesewege zu Cycloalkinen mittlerer Ringgröße Synthesis 1972 235-253.
    • (1972) Synthesis , pp. 235-253
    • Meier, H.1
  • 25
    • 0011877762 scopus 로고
    • Small rings with carbon-carbon triple bonds
    • G. Wittig Small rings with carbon-carbon triple bonds Angew. Chem., Int. Ed. Engl. 1962 1 415-419.
    • (1962) Angew. Chem., Int. Ed. Engl. , vol.1 , pp. 415-419
    • Wittig, G.1
  • 26
    • 0035249369 scopus 로고    scopus 로고
    • Synthesis of a macroheterocyclic compound through photodecarboxylation of potassium ω-phthalimidoalkynoate
    • D. J. Yoo E. Y. Kim M. Oelgemöller S. C. Shim Synthesis of a macroheterocyclic compound through photodecarboxylation of potassium ω-phthalimidoalkynoate Heterocycles 2001 54 1049-1055.
    • (2001) Heterocycles , vol.54 , pp. 1049-1055
    • Yoo, D.J.1    Kim, E.Y.2    Oelgemöller, M.3    Shim, S.C.4
  • 27
    • 0001427516 scopus 로고
    • A one step synthesis of ω-hydroxyacetylenic carboxylic acids
    • J. Cossy J. P. Pete A one step synthesis of ω-hydroxyacetylenic carboxylic acids Tetrahedron Lett. 1986 27 573-574.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 573-574
    • Cossy, J.1    Pete, J.P.2
  • 28
    • 0005594364 scopus 로고
    • Synthesis of acetylenic carboxylic acids
    • N. Gilman B. Holland Synthesis of acetylenic carboxylic acids Synth. Commun. 1974 4 199-201.
    • (1974) Synth. Commun. , vol.4 , pp. 199-201
    • Gilman, N.1    Holland, B.2
  • 30
    • 85077634689 scopus 로고
    • The use of diethylazodicarboxylate and triphenylphosphine in synthesis and transformations of natural products
    • O. Mitsunobu The use of diethylazodicarboxylate and triphenylphosphine in synthesis and transformations of natural products Synthesis 1981 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 31
    • 0000414496 scopus 로고
    • The Mitsunobu reaction
    • D. L. Hughes The Mitsunobu reaction J Org. React. 1992 42 335-656.
    • (1992) J Org. React. , vol.42 , pp. 335-656
    • Hughes, D.L.1
  • 32
    • 0001640928 scopus 로고    scopus 로고
    • Progress in the Mitsunobu reaction. A review
    • D. L. Hughes Progress in the Mitsunobu reaction. A review Org. Prep. Proced. Int. 1996 28 127-164.
    • (1996) Org. Prep. Proced. Int. , vol.28 , pp. 127-164
    • Hughes, D.L.1
  • 33
    • 0037344547 scopus 로고    scopus 로고
    • The photodecarboxylative addition of carboxylates to phthalimides: Scope and limitations
    • M. Oelgemöller P. Cygon J. Lex A. G. Griesbeck The photodecarboxylative addition of carboxylates to phthalimides: scope and limitations Heterocycles 2003 59 669-684.
    • (2003) Heterocycles , vol.59 , pp. 669-684
    • Oelgemöller, M.1    Cygon, P.2    Lex, J.3    Griesbeck, A.G.4
  • 34
    • 0040900045 scopus 로고    scopus 로고
    • Photodecarboxylative addition of carboxylates and α-keto carboxylates to phthalimides
    • A. G. Griesbeck M. Oelgemöller Photodecarboxylative addition of carboxylates and α-keto carboxylates to phthalimides Synlett 1999 492-494.
    • (1999) Synlett , pp. 492-494
    • Griesbeck, A.G.1    Oelgemöller, M.2
  • 36
  • 37
    • 0037149160 scopus 로고    scopus 로고
    • Photodecarboxylation study of carboxy-substituted N-alkylphthalimides in aqueous solution: Time resolved UV-Vis spectroscopy and conductometry
    • H. Görner M. Oelgemöller A. G. Griesbeck Photodecarboxylation study of carboxy-substituted N-alkylphthalimides in aqueous solution: time resolved UV-Vis spectroscopy and conductometry J. Phys. Chem. A 2002 106 1458-1464.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 1458-1464
    • Görner, H.1    Oelgemöller, M.2    Griesbeck, A.G.3
  • 38
    • 0032501457 scopus 로고    scopus 로고
    • In-cage formation of carbanions in photoinduced electron-transfer reaction of carboxylate ions
    • H. Yokoi T. Nakano W. Fujita K. Ishiguro Y. Sawaki In-cage formation of carbanions in photoinduced electron-transfer reaction of carboxylate ions J. Am. Chem. Soc. 1998 120 12453-12458.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 12453-12458
    • Yokoi, H.1    Nakano, T.2    Fujita, W.3    Ishiguro, K.4    Sawaki, Y.5
  • 39
    • 33845551459 scopus 로고
    • Conformational flexibility and photochemistry
    • P. J. Wagner Conformational flexibility and photochemistry Acc. Chem. Res. 1983 16 461-467.
    • (1983) Acc. Chem. Res. , vol.16 , pp. 461-467
    • Wagner, P.J.1
  • 40
    • 0033804280 scopus 로고    scopus 로고
    • The role of ring strain on the ease of ring closure of bifunctional chain molecules
    • For reviews, see
    • For reviews, see: C. Galli L. Mandolini The role of ring strain on the ease of ring closure of bifunctional chain molecules Eur. J. Org. Chem. 2000 3117-3125.
    • (2000) Eur. J. Org. Chem. , pp. 3117-3125
    • Galli, C.1    Mandolini, L.2
  • 41
    • 0029071193 scopus 로고
    • The syntheses of large-ring compounds
    • C. J. Roxburgh The syntheses of large-ring compounds Tetrahedron 1995 51 9767-9822.
    • (1995) Tetrahedron , vol.51 , pp. 9767-9822
    • Roxburgh, C.J.1
  • 42
    • 0001192434 scopus 로고
    • Cyclization and the conformation of hydrocarbon chains
    • M. A. Winnik Cyclization and the conformation of hydrocarbon chains Chem. Rev. 1981 81 491-524.
    • (1981) Chem. Rev. , vol.81 , pp. 491-524
    • Winnik, M.A.1
  • 43
    • 0029799845 scopus 로고    scopus 로고
    • Photochemical synthesis of macrocycles
    • A. G. Griesbeck A. Henz J. Hirt Photochemical synthesis of macrocycles Synthesis 1996 1261-1276.
    • (1996) Synthesis , pp. 1261-1276
    • Griesbeck, A.G.1    Henz, A.2    Hirt, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.