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Volumn 58, Issue 38, 2002, Pages 7595-7606

Investigations on photochemistry of o-allyloxy-/crotyloxyacetophenones: Formation of unexpected intramolecular arene-olefin addition products on n-π* excitation of ketones

Author keywords

1,5 biradical; Benzofuranols; Electron transfer; Hydrogen abstraction; Photochemistry; Photocycloadditions; Photoelectocyclization

Indexed keywords

2 ALLYLOXYACETOPHENONE; 2 CROTYLOXYACETOPHENONE; ACETONITRILE; ACETOPHENONE DERIVATIVE; ALCOHOL DERIVATIVE; ALKENE; BENZENE; DIHYDROBENZOFURAN DERIVATIVE; KETONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; TRIETHYLAMINE; UNCLASSIFIED DRUG;

EID: 0037119687     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00868-2     Document Type: Article
Times cited : (11)

References (74)
  • 13
    • 0000722346 scopus 로고
    • (a) De Keukeleire, He S.-L. Chem. Rev. 93:1993;359-380 (b) Ho T.-L. Distinctive Techniques in Organic Synthesis. 1998;World Scientific, Singapore. pp 284-378 (c) Horspool W.M., Synthetic Organic Photochemistry. 1984;Plenum, New York, (d) Crimmins M.T. Chem. Rev. 88:1988;1453-1473 (e) Mani J., Schuttel S., Zhang C., Bigler P., Muller C., Keesi R. Helv. Chim. Acta. 72:1989;487-495 (f) Oppolozer W. Acc. Chem. Res. 15:1982;135-141 (g) Watanbe H., Nakajima Y., Adachi M., Hotta H., Arai K., Baba Y., Noutray C., Ichikawa S., Kasumoto T., Hiyama T. J. Chem. Soc., Chem. Commun. 1999;1753-1754 (h) Randall M.L., Lo P.C.-K., Bonitatabus P.J. Jr., Snapper M.L. J. Am. Chem. Soc. 121:1999;4534-4535 (i) Dorr H., Rawal V.H. J. Am. Chem. Soc. 121:1999;10229-10230 (j) Zhang C., Bourgin D., Keese R. Tetrahedron. 47:1991;3059-3074 (k) Wagner P.J., Nahm K. J. Am. Chem. Soc. 109:1987;6528-6530 (l) Wagner P.J., Sakamoto M. J. Am. Chem. Soc. 111:1989;9254-9256 (m) Wagner P.J., Sakamoto M., Madkour A.E. J. Am. Chem. Soc. 114:1992;7298-7299.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7298-7299
    • Wagner, P.J.1    Sakamoto, M.2    Madkour, A.E.3
  • 17
    • 33845551459 scopus 로고
    • (a) Horspool W.M. Coyle J.D., Photochemistry in Organic Synthesis. 1986;61-79 Royal Society of Chemistry, Cambridge, (b) Wagner P.J. Acc. Chem. Res. 4:1971;168-177 (c) Scaiano J.C. Acc. Chem. Res. 15:1982;252-258 (d) Wagner P.J. Acc. Chem. Res. 16:1983;461-467.
    • (1983) Acc. Chem. Res. , vol.16 , pp. 461-467
    • Wagner, P.J.1
  • 31
    • 0005132208 scopus 로고
    • (a) Wagner P.J. Acc. Chem. Res. 22:1989;83-91 (b) Sharshira E.M., Shimada S., Okamura M., Hasegawa E., Horaguchi T. J. Heterocyl. Chem. 33:1996;1797-1805 (c) Sumathi T., Balasubramanian K.K. Tetrahedron Lett. 31:1990;3775-3778 (d) Pappas S.P., Zehr R.D. Jr. J. Am. Chem. Soc. 93:1971;7112-7113 (e) Sharshira E.M., Iwanami H., Okamura M., Hasegawa E., Horaguchi T. J. Heterocyl. Chem. 33:1996;137-144 (f) Sharshira E.M., Okamura M., Hasegawa E., Horaguchi T. J. Heterocyl. Chem. 34:1997;861-869 (g) Sharshira E.M., Horaguchi T. J. Heterocyl. Chem. 34:1997;1837-1849 (h) Wagner P.J., Meador M.A., Scaiano J.C. J. Am. Chem. Soc. 106:1984;7988-7989 (i) Wagner P.J., Jang J.-S. J. Am. Chem. Soc. 115:1993;7914-7915 (j) Wagner P.J., Meador M.A., Giri B.P., Scaiano J.C. J. Am. Chem. Soc. 107:1985;1087-1088 (k) Wagner P.J., Meador M.A., Park B.-S. J. Am. Chem. Soc. 112:1990;5199-5211 (l) Kraus G.A., Thomas P.J., Schwinden M.D. Tetrahedron Lett. 31:1990;1819-1822 (m) Pappas S.S., Pappas B.C., Blackwell J.E. Jr. J. Am. Chem. Soc. 89:1967;3066-3069.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 3066-3069
    • Pappas, S.S.1    Pappas, B.C.2    Blackwell J.E., Jr.3
  • 34
    • 33947086935 scopus 로고
    • (a) Wagner P.J., Thomas M.J., Harris E. J. Am. Chem. Soc. 98:1976;7675-7679 (b) Wagner P.J., Siebert. J. Am. Chem. Soc. 103:1981;7329-7335 (c) Wagner P.J., Kemppainen A.E., Schott H.N. J. Am. Chem. Soc. 95:1973;5604-5614.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 5604-5614
    • Wagner, P.J.1    Kemppainen, A.E.2    Schott, H.N.3
  • 37
    • 0001468390 scopus 로고    scopus 로고
    • (a) Clifford S., Bearpark M.J., Bernardi F., Olivucci M., Robb M.A., Smith B.R. J. Am. Chem. Soc. 118:1996;7353-7360 (b) Zand A., Park B.-S., Wagner. J. Org. Chem. 62:1997;2326-2327.
    • (1997) J. Org. Chem. , vol.62 , pp. 2326-2327
    • Zand, A.1    Park, B.-S.2    Wagner3
  • 38
    • 0005127206 scopus 로고    scopus 로고
    • 4l
    • 4l.
  • 44
  • 51
    • 0000215230 scopus 로고
    • (a) Gilbert A., Taylor G.N. J. Chem. Soc., Chem. Commun. 1979;229-230 (b) Wender P.A., Howbert J.J. J. Am. Chem. Soc. 103:1981;688-690 (c) Ellis-Davies G.C.R., Gilbert A., Heath P., Heath J.C., Lane J.C., Warrington J.V., Westover D.L. J. Chem. Soc., Perkin Trans. 2. 1984;1833-1841 (d) Neijenesch H.A., Ridderikhoff E.J., Ramsteijn C.A., Cornelisse J. J. Photochem. Photobiol. A: Chem. 48:1989;317-336 (e) Neijenesch H.A., de Ruiter R.J.P.J., Redderikhoff E.J., van den Ende J.O., Laarhoven L.J., van Putten K.J.W., Cornelisse J. J. Photochem. Photobiol. A: Chem. 60:1991;325-343.
    • (1991) J. Photochem. Photobiol. A: Chem. , vol.60 , pp. 325-343
    • Neijenesch, H.A.1    De Ruiter, R.J.P.J.2    Redderikhoff, E.J.3    Van den Ende, J.O.4    Laarhoven, L.J.5    Van Putten, K.J.W.6    Cornelisse, J.7
  • 54
    • 37049133830 scopus 로고
    • (a) Cohen S.G., Parola A., Parsons G.H. Jr. Chem. Rev. 1973;141-161 (b) Wu Z.-Z., Hug G.L., Morrison H. J. Am. Chem. Soc. 114:1992;1812-1816. and references cited therein (c) Guttenplan J.B., Cohen S.G. Chem. Commun. 1969;247-248.
    • (1969) Chem. Commun. , pp. 247-248
    • Guttenplan, J.B.1    Cohen, S.G.2
  • 58
    • 1542572036 scopus 로고
    • (a) Wagner P.J., Kelso P.A., Kemppainen A.E., McGrath J.M., Scott H.N., Zepp R.G. J. Am. Chem. Soc. 94:1972;7506-7512 (b) Yoon U.C., Mariano P.S. Acc. Chem. Res. 25:1992;233-240.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 233-240
    • Yoon, U.C.1    Mariano, P.S.2
  • 65
    • 0000100111 scopus 로고
    • (a) Hayward E.C., Tarbell D.S., Colebrook L.D. J. Org. Chem. 33:1968;399-402 (b) Mertes M.P., Powers L.J. J. Org. Chem. 36:1971;1805-1807 (c) Kozuka T. Bull. Chem. Soc. Jpn. 55:1982;2415-2423 (d) Suzuki T. Bull. Chem. Soc. Jpn. 58:1985;2821-2825 (e) Horaguchi T., Tsukada C., Hasegawa E., Shimizu T. J. Heterocyl. Chem. 28:1991;1261-1272.
    • (1991) J. Heterocyl. Chem. , vol.28 , pp. 1261-1272
    • Horaguchi, T.1    Tsukada, C.2    Hasegawa, E.3    Shimizu, T.4


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