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Volumn 37, Issue 33, 1996, Pages 5901-5904

Regio- and stereo-selective formation of 2-siloxy-2-alkoxyoxetanes in the photoreaction of cyclic ketene silyl acetals with 2-naphthaldehyde and their transformation to aldol-type adducts

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALDEHYDE DERIVATIVE; BICYCLO COMPOUND; KETENE DERIVATIVE; OXETANE DERIVATIVE; SILANE DERIVATIVE; SOLVENT;

EID: 0030581331     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01272-5     Document Type: Article
Times cited : (28)

References (22)
  • 1
    • 0000449533 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: New York
    • 1. For review, see; Porco, J. A.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991, vol. 5, 168-188.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 168-188
    • Porco, J.A.1    Schreiber, S.L.2
  • 2
    • 0001687114 scopus 로고
    • Horspool, W. M.; Song, P., Eds.; CRC Press: New York
    • 2. In Organic Photochemistry and Photobiology; Horspool, W. M.; Song, P., Eds.; CRC Press: New York, 1995, 522-569.
    • (1995) Organic Photochemistry and Photobiology , pp. 522-569
  • 7
    • 0022348217 scopus 로고
    • 4. A few examples for the regioselective formation of 2-alkoxy oxetanes have been reported in the reaction of β,β-dialkyl vinyl ethers, although the yields are low due to the competitive side-reactions, such as abstraction of an allylic hydrogen from the alkene by the excited carbonyl compounds, see; Bowers, K. G.; Mann, J. Tetrahedron Lett. 1985, 26, 4411.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 4411
    • Bowers, K.G.1    Mann, J.2
  • 8
    • 0004344770 scopus 로고
    • The Benjamin/Cummings Publishing Co., Inc.: Menlo Park
    • 5. Turro, N. J. In Modern Molecular Photochemistry; The Benjamin/Cummings Publishing Co., Inc.: Menlo Park, 1978, 432-452.
    • (1978) Modern Molecular Photochemistry , pp. 432-452
    • Turro, N.J.1
  • 9
    • 0000571518 scopus 로고
    • 6. Photo-induced electron transfer reactions of ketene silyl acetals were extensively studied by Fukuzumi et al., see; (a) Fukuzumi, S.; Fujita, M; Otera, J. J. Org. Chem. 1993, 58, 5405.
    • (1993) J. Org. Chem. , vol.58 , pp. 5405
    • Fukuzumi, S.1    Fujita, M.2    Otera, J.3
  • 11
    • 0029113157 scopus 로고
    • (b) Mikami, K.; Matsumoto, S.; Ishida, A.; Takamuku, S.; Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 1995, 117, 11134. See also, Mizuno, K.; Takahashi, N.; Nishiyama, T.; Inoue, H. Tetrahedron Lett. 1995, 36, 7463.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7463
    • Mizuno, K.1    Takahashi, N.2    Nishiyama, T.3    Inoue, H.4
  • 14
    • 85030211040 scopus 로고    scopus 로고
    • note
    • 3), readable signals δ 1.37, 18.44, 19.40, 21.49, 23.77, 49.43, 49.92, 51.10, 82.89, 115.99, 116.49.
  • 15
    • 0011942050 scopus 로고
    • 13C NMR signals with that of the analogous 2,2-diethoxyoxetane, see; Mattay, J.; Runsink, J. J. Org. Chem. 1985, 50, 2815.
    • (1985) J. Org. Chem. , vol.50 , pp. 2815
    • Mattay, J.1    Runsink, J.2
  • 16
    • 85030202613 scopus 로고    scopus 로고
    • note
    • 11. The acetonide 10 was obtained from the corresponding tri-ol prepared from 9 upon treatment with LAH.
  • 19
    • 0001492351 scopus 로고
    • 14. Structure of the proposed exciplex is not obvious. Formation of exciplex in the photoreactions of carbonyl compounds with electron-rich alkene is reported, see; Gersdorf, J.; Mattay, J.; Görner, H. J. Am. Chem. Soc. 1987, 109, 1203.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 1203
    • Gersdorf, J.1    Mattay, J.2    Görner, H.3
  • 20
    • 85030197838 scopus 로고    scopus 로고
    • note
    • .+).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.