2-Vinyl-1,1,2-trihalocyclopropanes - Valuable five carbon cyclopropane and cyclopropene synthetic intermediates

Tetrahedron

Volumn 52, Issue 33, 1996, Pages 10955-10968

  Al Dulayymi, Ahmad R ^a   Baird, Mark S ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030581414     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00592-3     Document Type: Article

References (18)

1. 1 Wendisch, D. Cyclopropene Derivatives, Carbocyclic Three-Ring Compounds, IV, Part 3, H. Weyl; Baird, M.S. Cyclopropene Derivatives, Carbocyclic Three-Ring Compounds, E17, H. Weyl in press. For an example see Franck-Neumann, M.; Dietrich-Buchecker, C. Tetrahedron Letts., 1980, 671.
2. 1 Wendisch, D. Cyclopropene Derivatives, Carbocyclic Three-Ring Compounds, IV, Part 3, H. Weyl; Baird, M.S. Cyclopropene Derivatives, Carbocyclic Three-Ring Compounds, E17, H. Weyl in press. For an example see Franck-Neumann, M.; Dietrich-Buchecker, C. Tetrahedron Letts., 1980, 671.
3. 1 Wendisch, D. Cyclopropene Derivatives, Carbocyclic Three-Ring Compounds, IV, Part 3, H. Weyl; Baird, M.S. Cyclopropene Derivatives, Carbocyclic Three-Ring Compounds, E17, H. Weyl in press. For an example see Franck-Neumann, M.; Dietrich-Buchecker, C. Tetrahedron Letts., 1980, 671.
4. 2. Halton, B.; Banwell, M.G. Cyclopropenes, in The Chemistry of Functional Groups, Cyclopropanes, Part 2, Wiley, 1987, 1223.
5. 3. Baird, M.S. Advances in Strain in Organic Chemistry, 1991, 1, 65.
6. 4. Billups, W.E.; Lin, L.-J. Tetrahedron, 1986, 42, 1575.
7. 5. Al Dulayymi, A.R., Al Dulayymi, J.R ; Baird, M.S.; Gerrard, M.E.; Koza, G.; Harkins, S.D.; Roberts, E. Tetrahedron, 1996, 52, 3409.
8. 6. D'yakonov, I.A. Zh.Obshch.Khim., 1961, 32, 664; D'yakonov, I.A.; Kornilova, TA.; Nizovkina, T.V. Zh.Org.Khim., 1967, 3, 273.
9. 6. D'yakonov, I.A. Zh.Obshch.Khim., 1961, 32, 664; D'yakonov, I.A.; Kornilova, TA.; Nizovkina, T.V. Zh.Org.Khim., 1967, 3, 273.
10. 7. Baird, M.S.; Roberts, E.; Al Dulayymi, A.R. unpublished results.
11. 8. Baird, M.S.; Hussain, H.H.; Nethercott, W., J.Chem.Soc, Perkin Trans.I., 1986, 1845.
12. 9. Apeliog, Y.; Arad, D.; Kapon, M.; Warrerstein, M. Tetrahedron Letts., 1987, 5917; Muller, P.; Bernardinelli, G.; Pyffer, J.; Rodriguez, D.; Schaller, J.-P. Helv.Chim.Acta, 1988, 71, 544.
13. 9. Apeliog, Y.; Arad, D.; Kapon, M.; Warrerstein, M. Tetrahedron Letts., 1987, 5917; Muller, P.; Bernardinelli, G.; Pyffer, J.; Rodriguez, D.; Schaller, J.-P. Helv.Chim.Acta, 1988, 71, 544.
14. 10. Maier, H.; Norbert, H.; Molz, T.; Bissinger, H.; Kolshorn, H. Tetrahedron, 1986, 42, 1711.
15. 11. Crossland, I. Acta Chem.Scand., 1975, B29, 468; Holm, T.; Crossland, I. Acta Chem.Scand., 1979, B33, 421. We thank the referee for drawing our attention to these observations.
16. 11. Crossland, I. Acta Chem.Scand., 1975, B29, 468; Holm, T.; Crossland, I. Acta Chem.Scand., 1979, B33, 421. We thank the referee for drawing our attention to these observations.
17. 2,4]hexanes by dimerisation of transient 1-alkenylcyclopropene-3-carboxylates has been decribed [Shapiro, E. A.; Kalinin, A.V.; Ugrak, B.I.; Nefedov, O.M. J.Chem.Soc., Perkin Trans.II, 1994, 709] while a 1-alkenyl-2-trimethylsilylcyclopropene-3-carboxylate may be isolated [ Shapiro, E.A.; Kalinin, A.V.; Platonov, D.N.; Nefedov, O.M. Izv.Akad.Nauk SSSR, Ser.Khim., 1993, 1248.
18. 2,4]hexanes by dimerisation of transient 1-alkenylcyclopropene-3-carboxylates has been decribed [Shapiro, E. A.; Kalinin, A.V.; Ugrak, 1B.I.; Nefedov, O.M. J.Chem.Soc., Perkin Trans.II, 1994, 709] while a 1-alkenyl-2-trimethylsilylcyclopropene-3-carboxylate may be isolated [ Shapiro, E.A.; Kalinin, A.V.; Platonov, D.N.; Nefedov, O.M. Izv.Akad.Nauk SSSR, Ser.Khim., 1993, 1248.