메뉴 건너뛰기




Volumn 76, Issue 3, 2003, Pages 635-641

Deoxygenative dimerization of benzylic and allylic alcohols, and their ethers and esters using lanthanum metal and chlorotrimethylsilane in the presence of a catalytic amount of iodine and copper(I) iodide

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COPPER COMPOUNDS; DIMERIZATION; ESTERS; ETHERS; IODINE; LANTHANUM; SILANES;

EID: 0037251839     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.76.635     Document Type: Article
Times cited : (20)

References (71)
  • 1
    • 0001343212 scopus 로고
    • For recent reviews: a) H. B. Kagan, New J. Chem., 14, 453 (1990).
    • (1990) New J. Chem. , vol.14 , pp. 453
    • Kagan, H.B.1
  • 12
    • 33847086035 scopus 로고
    • and Ref. 1 and references cited therein
    • P. Girard, J. L. Namy, and H. B. Kagan, J. Am. Chem. Soc., 102, 2693 (1980) and Ref. 1 and references cited therein.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2693
    • Girard, P.1    Namy, J.L.2    Kagan, H.B.3
  • 13
    • 0001175493 scopus 로고
    • and Ref. 1i and references cited therein
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • (1995) Rev. Heteroatom Chem. , vol.12 , pp. 163
    • Taniguchi, Y.1    Takaki, K.2    Fujiwara, Y.3
  • 14
    • 0012796954 scopus 로고    scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • Chem. Lett. , vol.1994 , pp. 1279
    • Yanada, R.1    Bessho, K.2    Yanada, K.3
  • 15
    • 14744295576 scopus 로고    scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • Synlett , vol.1995 , pp. 443
    • Yanada, R.1    Bessho, K.2    Yanada, K.3
  • 16
    • 85061411950 scopus 로고    scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • Synlett , vol.1995 , pp. 1261
    • Yanada, R.1    Negoro, N.2    Bessho, K.3    Yanada, K.4
  • 17
    • 0030599660 scopus 로고    scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9313
    • Yanada, R.1    Negoro, N.2    Yanada, K.3    Fujita, T.4
  • 18
    • 0030944453 scopus 로고    scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3271
    • Yanada, R.1    Negoro, N.2    Yanada, K.3    Fujita, T.4
  • 19
    • 0347846816 scopus 로고    scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • (1997) Youji Huaxue , vol.17 , pp. 165
    • Ding, Z.-B.1    Wu, S.-H.2
  • 20
    • 0032505187 scopus 로고    scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • (1998) Tetrahedron , vol.54 , pp. 11129
    • Wang, L.1    Zhang, Y.2
  • 21
    • 0035847217 scopus 로고    scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • (2001) J. Org. Chem. , vol.66 , pp. 330
    • Talukdar, S.1    Fang, J.-M.2
  • 22
    • 0000122684 scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • (1982) Tetrahedron Lett. , vol.23 , pp. 1353
    • Imamoto, T.1    Kusumoto, T.2    Hatanaka, Y.3    Yokoyama, M.4
  • 23
    • 0012811130 scopus 로고    scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • J. Chem. Soc., Chem. Commun. , vol.1986 , pp. 475
    • Fukuzawa, S.1    Fujinami, T.2    Sakai, S.3
  • 24
    • 0000849612 scopus 로고
    • Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
    • (1990) J. Org. Chem. , vol.55 , pp. 1628
    • Fukuzawa, S.1    Sumimoto, N.2    Fujinami, T.3    Sakai, S.4
  • 31
    • 0000817472 scopus 로고
    • ed by B. M. Trost and I. Fleming, Pergamon Press
    • a) R. Bohlmann, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, (1991), Vol. 6, pp. 203-223.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 203-223
    • Bohlmann, R.1
  • 40
    • 0000167214 scopus 로고
    • It is already known that the reaction of alcohols with iodotrimethylsilane forms the corresponding iodides in good yields. See: M. E. Jung and P. L. Ornstein, Tetrahedron Lett., 31, 2659 (1977).
    • (1977) Tetrahedron Lett. , vol.31 , pp. 2659
    • Jung, M.E.1    Ornstein, P.L.2
  • 41
    • 0003686469 scopus 로고
    • 3SiI equivalent and used as a versatile reagent for the conversion of alcohols into organoiodide compounds. See: a) G. A. Olah, S. C. Narang, B. G. B. Gupta, and R. Malhotra, J. Org. Chem., 44, 1247 (1979). b) T. Sakai, K. Miyata, M. Utaka, and A. Takeda, Tetrahedron Lett., 28, 3817 (1987). c) T. Sakai, K. Miyata, S. Tsuboi, A. Takeda, M. Utaka, and S. Torii, Bull. Chem. Soc. Jpn., 62, 3537 (1989). d) S. Irifune, T. Kibayashi, Y. Ishii, and M. Ogawa, Synthesis, 1988, 366. e) T. Kanai, S. Irifune, Y. Ishii, and M. Ogawa, Synthesis, 1989, 283.
    • (1979) J. Org. Chem. , vol.44 , pp. 1247
    • Olah, G.A.1    Narang, S.C.2    Gupta, B.G.B.3    Malhotra, R.4
  • 42
    • 0000089612 scopus 로고
    • 3SiI equivalent and used as a versatile reagent for the conversion of alcohols into organoiodide compounds. See: a) G. A. Olah, S. C. Narang, B. G. B. Gupta, and R. Malhotra, J. Org. Chem., 44, 1247 (1979). b) T. Sakai, K. Miyata, M. Utaka, and A. Takeda, Tetrahedron Lett., 28, 3817 (1987). c) T. Sakai, K. Miyata, S. Tsuboi, A. Takeda, M. Utaka, and S. Torii, Bull. Chem. Soc. Jpn., 62, 3537 (1989). d) S. Irifune, T. Kibayashi, Y. Ishii, and M. Ogawa, Synthesis, 1988, 366. e) T. Kanai, S. Irifune, Y. Ishii, and M. Ogawa, Synthesis, 1989, 283.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3817
    • Sakai, T.1    Miyata, K.2    Utaka, M.3    Takeda, A.4
  • 43
    • 0024793690 scopus 로고
    • 3SiI equivalent and used as a versatile reagent for the conversion of alcohols into organoiodide compounds. See: a) G. A. Olah, S. C. Narang, B. G. B. Gupta, and R. Malhotra, J. Org. Chem., 44, 1247 (1979). b) T. Sakai, K. Miyata, M. Utaka, and A. Takeda, Tetrahedron Lett., 28, 3817 (1987). c) T. Sakai, K. Miyata, S. Tsuboi, A. Takeda, M. Utaka, and S. Torii, Bull. Chem. Soc. Jpn., 62, 3537 (1989). d) S. Irifune, T. Kibayashi, Y. Ishii, and M. Ogawa, Synthesis, 1988, 366. e) T. Kanai, S. Irifune, Y. Ishii, and M. Ogawa, Synthesis, 1989, 283.
    • (1989) Bull. Chem. Soc. Jpn. , vol.62 , pp. 3537
    • Sakai, T.1    Miyata, K.2    Tsuboi, S.3    Takeda, A.4    Utaka, M.5    Torii, S.6
  • 44
    • 0002816673 scopus 로고    scopus 로고
    • 3SiI equivalent and used as a versatile reagent for the conversion of alcohols into organoiodide compounds. See: a) G. A. Olah, S. C. Narang, B. G. B. Gupta, and R. Malhotra, J. Org. Chem., 44, 1247 (1979). b) T. Sakai, K. Miyata, M. Utaka, and A. Takeda, Tetrahedron Lett., 28, 3817 (1987). c) T. Sakai, K. Miyata, S. Tsuboi, A. Takeda, M. Utaka, and S. Torii, Bull. Chem. Soc. Jpn., 62, 3537 (1989). d) S. Irifune, T. Kibayashi, Y. Ishii, and M. Ogawa, Synthesis, 1988, 366. e) T. Kanai, S. Irifune, Y. Ishii, and M. Ogawa, Synthesis, 1989, 283.
    • Synthesis , vol.1988 , pp. 366
    • Irifune, S.1    Kibayashi, T.2    Ishii, Y.3    Ogawa, M.4
  • 45
    • 84987488555 scopus 로고    scopus 로고
    • 3SiI equivalent and used as a versatile reagent for the conversion of alcohols into organoiodide compounds. See: a) G. A. Olah, S. C. Narang, B. G. B. Gupta, and R. Malhotra, J. Org. Chem., 44, 1247 (1979). b) T. Sakai, K. Miyata, M. Utaka, and A. Takeda, Tetrahedron Lett., 28, 3817 (1987). c) T. Sakai, K. Miyata, S. Tsuboi, A. Takeda, M. Utaka, and S. Torii, Bull. Chem. Soc. Jpn., 62, 3537 (1989). d) S. Irifune, T. Kibayashi, Y. Ishii, and M. Ogawa, Synthesis, 1988, 366. e) T. Kanai, S. Irifune, Y. Ishii, and M. Ogawa, Synthesis, 1989, 283.
    • Synthesis , vol.1989 , pp. 283
    • Kanai, T.1    Irifune, S.2    Ishii, Y.3    Ogawa, M.4
  • 48
    • 85038477693 scopus 로고    scopus 로고
    • note
    • When 5 was added to the solution, in which copper(I) iodide was treated with 1/3 molar amount of lanthanum metal, the reductive dimerization was not accelerated. On the basis of the result, the reaction pathway including the formation of lanthanum-copper-combined active reducing species cannot be ruled out at the present time.
  • 49
    • 85038471448 scopus 로고    scopus 로고
    • note
    • Various highly reactive metals have been prepared and used for various reactions. See: Ref. 13 and references cited therein.
  • 50
    • 85038470442 scopus 로고    scopus 로고
    • note
    • On the iodination of alcohols with chlorotrimethylsilane/sodium iodide reagent, it was reported that the reaction of benzylic or allylic alcohols was faster than that of aliphatic alcohols. See: Ref. 12a
  • 51
    • 85038477238 scopus 로고    scopus 로고
    • note
    • In the case of primary and secondary aliphatic alcohols, lanthanum metal was completely consumed even if no coupling reaction proceeded.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.