1,2,2-Tribromocyclopropanecarboxylic acid and derivatives - Valuable intermediates for four carbon cyclopropane and cyclopropene synthons

Tetrahedron

Volumn 52, Issue 10, 1996, Pages 3409-3424

  Al Dulayymi, Ahmad R ^a   Al Dulayymi, Juma'a R ^a   Baird, Mark S ^a   Gerrard, Michelle E ^a   Koza, Gani ^a   Harkins, Samantha D ^a   Roberts, Evan ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030050960     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01123-4     Document Type: Article

References (44)

1. We thank SERC and Shell Research for the Award of a CASE studentship to MEG; this work was carried out in the Department of Chemistry, University of Newcastle upon Tyne.
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3. Wendisch, D. Cyclopropene Derivatives, Carbocyclic Three-Ring Compounds, Vol. IV, Part 3, H.Weyl; Baird, M.S. Cyclopropene Derivatives, Carbocyclic Three-Ring Compounds, E17, H.Weyl in press.
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36. Baird, M.S.; Bolesov, I.G. Eliminations involving carbon-halogen bonds and leading to highly strained rings, in The Chemistry of Functional Groups, Ed. Patai, S.; Rappoport, Z. Wiley, 1995; Al Dulayymi, J.R.; Baird, M.S. Tetrahedron Lett., 1988, 6147, Nilsen, N.O.; Skattebol, L.; Baird, M.S.; Buxton, S.R.; Slowey, P.D. Tetrahedron Lett., 1984, 2887.
37. Baird, M.S.; Bolesov, I.G. Eliminations involving carbon-halogen bonds and leading to highly strained rings, in The Chemistry of Functional Groups, Ed. Patai, S.; Rappoport, Z. Wiley, 1995; Al Dulayymi, J.R.; Baird, M.S. Tetrahedron Lett., 1988, 6147, Nilsen, N.O.; Skattebol, L.; Baird, M.S.; Buxton, S.R.; Slowey, P.D. Tetrahedron Lett., 1984, 2887.
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39. The related aldehyde, 1,1-dibromo-2-chloro-2-formylcyclopropane is readily obtained by the ozonolysis of the 1,1-dibromo-2-chloro-2-vinylcyclopropane, the dibromocarbene adduct of chloroprene followed by work up with dimethylsulphide (Al Dulayymi, A.R. unpublished results).
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42. H 7.7 (1H, s),3.45 (1 H, d, J 10.6 Hz), 3.3 - 3.4 (m, 3 H), 0.5 (1H, dd, J 3.7, 10.1 Hz), 0.4 (1 H, dd, J 3.7, 7.8 Hz), -0.01 (9 H, s), -0.53 (1H, dd, J 7.8, 10.1 Hz). The stereochemistry of (29) is assigned provisionally on the basis of an endo-transition state controlled by the size of the silyl-substituents (Baird, M.S.; Hussain, H.H.; Clegg, W. J.Chem.Res., 1988, 110S).
43. H 7.7 (1H, s),3.45 (1 H, d, J 10.6 Hz), 3.3 - 3.4 (m, 3 H), 0.5 (1H, dd, J 3.7, 10.1 Hz), 0.4 (1 H, dd, J 3.7, 7.8 Hz), -0.01 (9 H, s), -0.53 (1H, dd, J 7.8, 10.1 Hz). The stereochemistry of (29) is assigned provisionally on the basis of an endo-transition state controlled by the size of the silyl-substituents (Baird, M.S.; Hussain, H.H.; Clegg, W. J.Chem.Res., 1988, 110S).
44. H 7.7 (1H, s),3.45 (1 H, d, J 10.6 Hz), 3.3 - 3.4 (m, 3 H), 0.5 (1H, dd, J 3.7, 10.1 Hz), 0.4 (1 H, dd, J 3.7, 7.8 Hz), -0.01 (9 H, s), -0.53 (1H, dd, J 7.8, 10.1 Hz). The stereochemistry of (29) is assigned provisionally on the basis of an endo-transition state controlled by the size of the silyl-substituents (Baird, M.S.; Hussain, H.H.; Clegg, W. J.Chem.Res., 1988, 110S).