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Volumn 2002, Issue 7, 2002, Pages 197-211

Cascade radical cyclization of polyolefinic vinyl iodides: Comparisonbetween 5-exo and 6-endo cyclization of vinyl radicals

Author keywords

Cascade reaction; Polycyclic systems; Radical reaction; Regioselectivity; Vinyl radicals

Indexed keywords

1 IODO 1,5,10 TRIENE; 1 IODO 1,5,9,14 TETRAENE; 10 TERT BUTYLDIMETHYLSILOXY 1 IODO 5 METHYL 1,5 DECADIENE; 11 METHOXYCARBONYLMETHYL 2,10 DIMETHYLTRICYCLO[8.4.0.0 2,7 ]TETRADEC 5 ENE; ALKENE DERIVATIVE; CYCLOALKANE; CYCLOALKENE; METHYL 16 IODO 8,12 DIMETHYL 2,7,11,15 HEXADECATETRAENOATE; METHYL 8 METHYL 11 (1 METHYL 2 CYCLOPENTENYL) 2,7 UNDECADIENOATE; POLYENE; TRIMETHYL 1 IODO 5 METHYLUNDECA 1,5,10 TRIENE 8,8,11 TRICARBOXYLATE; TRIMETHYL 1 METHYLTRICYCLO[6.3.0.0 2,6 ]UNDECANE 4,4,7 TRICARBOXYLATE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 3242664389     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (6)

References (33)
  • 2
    • 0001216647 scopus 로고
    • ed. by Trost, B. M.; Fleming, I. and Semmelhack, M. F.; Pergamon, Oxford
    • (b) Curran, D. P. in Comprehensive Organic Synthesis, ed. by Trost, B. M.; Fleming, I. and Semmelhack, M. F.; Pergamon, Oxford, 1991, Vol. 4, P. 715.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 715
    • Curran, D.P.1
  • 30
    • 3242700108 scopus 로고    scopus 로고
    • note
    • -1 absorption (C=O) in IR spectrum (neat).
  • 31
    • 84970560674 scopus 로고
    • Previously, Curran depicted the radical reaction of analogous 1-iodo-1,5,10-triene. However, the reaction was unsatisfactory resulted in the production of tricyclo[6.3.0.0]undecane as an inseparable mixture of four diastereomers and another isomers. Curran, D. P.; Sun, S. Aust. J. Chem. 1995, 48, 261-267.
    • (1995) Aust. J. Chem. , vol.48 , pp. 261-267
    • Curran, D.P.1    Sun, S.2
  • 32
    • 3242677489 scopus 로고    scopus 로고
    • note
    • The reaction of tertiary alkyl radicals with intramolecular di- and tri-substituted olefin usually predominates 6-endo-trig cyclization over 5-exo-trig one. See ref. 3a.
  • 33
    • 33646230522 scopus 로고
    • In the second cyclization of 27, the rate of 5-exo-trig cyclization might be ∼100 times faster than 3-exo-trig cyclization, which can lead to homoallyl-homoallyl radical rearrangement. For a review of kinetics of radical cyclizations, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323.
    • (1980) Acc. Chem. Res. , vol.13 , pp. 317-323
    • Griller, D.1    Ingold, K.U.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.