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Volumn 74, Issue 22, 2009, Pages 8726-8732

Two approaches to diverting the course of a free-radical cyclization: Application of cyclopropylcarbinyl radical fragmentations and allenes as radical acceptors

Author keywords

[No Author keywords available]

Indexed keywords

ALLENES; ATOM TRANSFER; CHEMICAL EQUATIONS; RADICAL ACCEPTORS; RADICAL CYCLIZATIONS; RADICAL FRAGMENTATION; REDUCTION PRODUCTS; SECONDARY CYCLIZATION;

EID: 70449670732     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901834q     Document Type: Article
Times cited : (12)

References (44)
  • 3
    • 37049066358 scopus 로고
    • For a radical cyclization-atom transfer-radical cyclization sequence related to that encountered in this work, see
    • For a radical cyclization-atom transfer-radical cyclization sequence related to that encountered in this work, see: Clive, D. L. J.; Khodabocus, A.; Cantin, M.; Tao, Y. J. Chem. Soc., Chem. Commun. 1991, 1755-1757.
    • (1991) J. Chem. Soc., Chem. Commun. , pp. 1755-1757
    • Clive, D.L.J.1    Khodabocus, A.2    Cantin, M.3    Tao, Y.4
  • 4
    • 0033610461 scopus 로고    scopus 로고
    • For lead references on the structures and/or synthesis of polyandranes, see
    • For lead references on the structures and/or synthesis of polyandranes, see: Walker, D. P.; Grieco, P. A. J. Am. Chem. Soc. 1999, 121, 9891- 9892.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9891-9892
    • Walker, D.P.1    Grieco, P.A.2
  • 8
    • 2342524627 scopus 로고    scopus 로고
    • For earlier publications in this series, see
    • For earlier publications in this series, see: Donahue, M. G.; Hart, D. J. Can. J. Chem. 2004, 82, 314-317.
    • (2004) Can. J. Chem. , vol.82 , pp. 314-317
    • Donahue, M.G.1    Hart, D.J.2
  • 10
    • 33750040568 scopus 로고    scopus 로고
    • For a preliminary account of work shown in Schemes 1 and 2, see
    • For a preliminary account of work shown in Schemes 1 and 2, see: Cwynar, V.; Donahue, M. G.; Hart, D. J.; Yang, D. Org. Lett. 2006, 8, 4577-4580.
    • (2006) Org. Lett. , vol.8 , pp. 4577-4580
    • Cwynar, V.1    Donahue, M.G.2    Hart, D.J.3    Yang, D.4
  • 11
    • 70449684555 scopus 로고    scopus 로고
    • note
    • 3SnH were 10 and 100 mM, respectively (see the Supporting Information for details of the cyclizations shown in Schemes 1 and 2).
  • 22
    • 70449680694 scopus 로고    scopus 로고
    • note
    • Compounds 26 and 27 were characterized as a mixture. Manipulation of this mixture provided compounds 26 (free of 27) as a mixture (see the Supporting Information for details).
  • 26
    • 70449649142 scopus 로고    scopus 로고
    • note
    • Omission of theK2CO3 (acid sponge) resulted in formation of a large number of products.
  • 27
    • 70449647607 scopus 로고    scopus 로고
    • note
    • Alcohol 40 was sensitive and was used in the subsequent free-radical cyclization on the same day it was prepared.
  • 33
    • 0000163018 scopus 로고
    • For radical cyclizations in which allenes are the acceptor, see
    • For radical cyclizations in which allenes are the acceptor, see: Apparu, M.; Crandall, J. K. J. Org. Chem. 1984, 49, 2125-2130.
    • (1984) J. Org. Chem. , vol.49 , pp. 2125-2130
    • Apparu, M.1    Crandall, J.K.2
  • 34
    • 0001562822 scopus 로고
    • Hart, D. J. Science 1984, 223, 883-887.
    • (1984) Science , vol.223 , pp. 883-887
    • Hart, D.J.1
  • 38
    • 64349122718 scopus 로고    scopus 로고
    • It is also possible that the slow rate at which allylic radicals undergo hydrogen atom transfer may also contribute to the success of this strategy. For some relevant references, see
    • It is also possible that the slow rate at which allylic radicals undergo hydrogen atom transfer may also contribute to the success of this strategy. For some relevant references, see: Hayes, C. J.; Burgess, D. R. Jr. J. Phys. Chem.A2009, 113, 2473-2482.
    • (2009) J. Phys. Chem.A , vol.113 , pp. 2473-2482
    • Hayes, C.J.1    Burgess Jr., D.R.2
  • 41
    • 37049145470 scopus 로고
    • For strain in bicyclo[3.3.0]octanes, see
    • For strain in bicyclo[3.3.0]octanes, see: Barrett, J. W.; Linstead, R. P. J. Chem. Soc. 1935, 436-442.
    • (1935) J. Chem. Soc. , pp. 436-442
    • Barrett, J.W.1    Linstead, R.P.2
  • 43
    • 70449677071 scopus 로고    scopus 로고
    • note
    • Tri-n-butyltin hydride mediated cyclization of 7-epi-49 provided 7-epi-52 (mp 101-105 °C) in 63% yield. The structure of this compound was established by X-ray crystallography.
  • 44
    • 84980127075 scopus 로고
    • Prepared from commercially available chloromethyl pivalate using a Finkelstein reaction (36 mmol of chloromethyl pivalate and 54 mmol of sodium iodide in 40mL of acetone at roomtemperature for 12 h) and used within 24 h
    • Prepared from commercially available chloromethyl pivalate using a Finkelstein reaction (36 mmol of chloromethyl pivalate and 54 mmol of sodium iodide in 40mL of acetone at roomtemperature for 12 h) and used within 24 h: Finkelstein, H. Chem. Ber. 1910, 43, 1528-1532.
    • (1910) Chem. Ber. , vol.43 , pp. 1528-1532
    • Finkelstein, H.1


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