Access to cyclopropyl cations via carbene fragmentation

Tetrahedron Letters

Volumn 45, Issue 16, 2004, Pages 3321-3326

  Moss, Robert A ^a   Chu, Gaosheng ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRINE DERIVATIVE; CARBENE; CATION; CYCLOPROPANE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION KINETICS; EVAPORATION; FRAGMENTATION REACTION; GEL CHROMATOGRAPHY; OXIDATION KINETICS; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 1642603913     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.046     Document Type: Article

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25. 3): 1.22 (t, J=7 Hz, 1H, ring CH), 1.32 (s, 3H, Me), 1.51 (m, 1H, ring CH), 2.65 (dd, J=7.2, 2.8 Hz, 1H, PhCH), 7.1-7.4 (m, 5H, Ph). Z-32 : 1.28 (m, 1H, ring CH), 1.47 (t, J=7 Hz, 1H, ring CH), 1.77 (s, 3H, Me), 2.17 (t, J=8 Hz, PhCH), 7.15-7.35 (m, 5H, Ph).
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27. 2Cl), 6.52 (s, 1H, vinyl CH), 7.18-7.30 (m, 5H, Ph).
28. 3), 5.00 (s, 1H, PhCHCl), 5.17 (s, 1H, vinyl CH), 5.48 (s, 1H, vinyl CH), 7.2-7.3 (m, 5H, Ph).
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36. For example, fragmentation of trans-2-phenyl-1- cyclopropyloxychlorocarbene in DCE affords 12% of trans-2-phenyl-1- chlorocyclopropane, 9% of cis-2-phenyl-1-chlorocyclopropane, 11% of trans-1-phenyl-3-chloro-1-propene, 19% of 3-chloro-3-phenylpropene, 41% of the dichloride due to HCl capture of the carbene, and 8% of the formate due to water capture of the carbene.
37. 3. Residual pentane was then removed by rotary evaporation at 0 °C. The yield of 13 was approximately 25%, based on 1-cyclopropyl-1-cyclopropanol.