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Volumn 74, Issue 15, 2009, Pages 5595-5598

An X- (X = I, Br)-triggered ring-opening cyclization of cyclopropenyl-substituted alkyl halides or mesylates: An efficient and highly regioand stereoselective approach to (E)-haloalkylidene 4-7-membered cyclic compounds

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL HALIDES; C-C BONDS; CARBON-HALOGEN BOND; CHEMICAL EQUATIONS; CYCLIC COMPOUNDS; CYCLIC PRODUCTS; CYCLOPROPENES; INTRAMOLECULAR TRAPPING; MESYLATES; RING OPENING; STEREO-SELECTIVE;

EID: 68049089947     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900389m     Document Type: Article
Times cited : (22)

References (77)
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    • For some representative reports on the ring-opening reactions of alkylidenecyclopropanes, see: a
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    • For some representative reports on the reactions C=C bond on cyclopropenes, see: (a) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978 and references cited therein.
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    • Crystal data for compound E-2a: C16H 17O4I, MW, 400.20, monoclinic, space group P2(1)/c, final R indices [I > 2σ(I, R1, 0.0332, wR2, 0.0847, R indices (all data, R1, 0.0394, wR2, 0.0878, a, 9.1568 (7) Å, b, 19.9575 (16) Å, c, 9.6108 (7) Å, α, 90°, β, 114.2340(1)°, γ, 90°, V, 1601.6 (2) Å3, T, 293(2) K, Z, 4, reflections collected/unique: 9277/3483 (R(int, 0.0446, number of observations [> 2σ(I, 2984, parameters 193. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 694977. Copies of the data can be obtained free of charge on application toCCDC, 12 Union Road, Cambridge CB2 1EZ, UK Fax:, 44-1223/336- 033; E-mail: deposit@ccdc.cam.ac.uk
    • 3, T = 293(2) K, Z = 4, reflections collected/unique: 9277/3483 (R(int) = 0.0446), number of observations [> 2σ(I)] 2984, parameters 193. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 694977. Copies of the data can be obtained free of charge on application toCCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: + 44-1223/336- 033; E-mail: deposit@ccdc.cam.ac.uk).
  • 76
    • 68049098624 scopus 로고    scopus 로고
    • Crystal data for compound E-2b: C12H 17O4I, MW, 352.16, monoclinic, space group P2(1)/c, final R indices [I > 2σ(I, R1, 0.0416, wR2, 0.1048, R indices (all data, R1, 0.0460, wR2, 0.1075, a, 8.2163(9) Å, b, 13.1526(15) Å, c, 12.5835(14) Å, α, 90°, β, 95.994(2)°, γ, 90°, V, 1352.4 (3) Å3, T, 293(2) K, Z, 4, reflections collected/unique: 7777/2944 (R(int, 0.0900, number of observations [> 2σ(I, 2565, parameters 157. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 694978. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK Fax:, 44-1223/336- 033; E-mail: deposit@ccdc.cam.ac.uk
    • 3, T = 293(2) K, Z = 4, reflections collected/unique: 7777/2944 (R(int) = 0.0900), number of observations [> 2σ(I )] 2565, parameters 157. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 694978. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: + 44-1223/336- 033; E-mail: deposit@ccdc.cam.ac.uk).


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