Kinetic study of dichlorocyclopropanation of 1,7-octadiene under two-phase phase-transfer catalysis at low alkaline concentration

Journal of Molecular Catalysis A: Chemical

Volumn 198, Issue 1-2, 2003, Pages 111-124

  Wang, Maw Ling ^a   Hsieh, Yu Ming ^b   Chang, Rong Yeu ^b  

^a TUNGHAI UNIVERSITY   (Taiwan)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

Dichlorocarbene; Dichlorocyclopropanation; Interfacial reaction; Phase transfer catalysis

Indexed keywords

CATALYSIS; PHASE TRANSITIONS; REACTION KINETICS; SALTS; SOLVENTS;

PHASE-TRANSFER CATALYTIC (PTC) REACTIONS;

AMMONIUM COMPOUNDS;

1,7 OCTADIENE; ALKENE DERIVATIVE; CARBENOID; CHLOROFORM; DICHLOROCARBENE; ORGANIC SOLVENT; QUATERNARY AMMONIUM DERIVATIVE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ALKALINITY; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; CONCENTRATION RESPONSE; CYCLOPROPANATION; DICHLOROCYCLOPROPANATION; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR MODEL; PHASE TRANSITION; PRECURSOR; REACTION ANALYSIS; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 0038669194     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(03)00005-0     Document Type: Article

References (17)

1. C.M. Starks, C.L. Liotta, M. Halpern, Phase Transfer Catalysis, Fundamentals, Applications and Industrial Perspectives, Chapman & Hall, New York, 1994.
2. E.V. Dehmlow, S.S. Dehmlow, Phase Transfer Catalysis, VEB Chemie, Weinheim, Germany, 1983.
3. W.P. Weber, G.W. Gokel, Phase Transfer Catalysis in Organic Chemistry, Springer, New York, 1977.
4. H.H. Freedman, Industrial applications of phase transfer catalysis (PTC): past, present and future, Pure Appl. Chem. 58 (6) (1986) 857-868.
5. W.E. Doering, A.K. Hoffmann, The addition of dichlorocarbene to olefin, J. Am. Chem. Soc. 76 (1954) 6162-6165.
6. E.P. William, E.S. Edward, Halocyclopropanes from halocarbenes, Organic Reactions 13 (1971) 55-90.
7. M. Makosza, M. Wawrzyniewicz, Reactions of organic anions. Part XXIV. Catalytic method for preparation of dichlorocyclopropane derivatives in aqueous medium, Tetrahedron Lett. 53 (1969) 4659-4662.
8. M. Makosza, M. Fedroynski, Improved method of dibromocycloprpoane derivatives, Synth. Comm. 3 (4) (1973) 305-309.
9. M. Makosza, New results in the mechanism and application of phase-transfer catalysis, ACS Symp. Ser. 695 (1996) 41-51.
10. E.V. Dehmlow, M. Prashad, Applications of phase transfer catalysis. Part 25. Selectivity of dichlorocyclopropanations by phase transfer catalysis, J. Chem. Res. (S) (1982) 354-355.
11. T. Hiyama, H. Sawada, M. Tasukanaka, H. Nozaki, β-Hydroxyethyltrialkylammonium ion as a selective phase-transfer catalyst for dihalocyclopropanation, Tetrahedron Lett. 34 (1975) 3013-3016.
12. S. Julia, A. Ginebreda, A new method for the generation of dichlorocarbene using solid-liquid phase transfer catalysis, Synthesis (1977) 682-683.
13. E.W. Dehmlow, J. Wilkenloh, Applications of phase-transfer catalysis. Part 29. Dibromocarbene addition - hydrolysis competition in the presence of concentrated sodium hydroxide, J. Chem. Res. (S) (1984) 396-397.
14. E. Nomura, H. Taniguchi, Y. Otsuji, Carlixarene - catalyzed generation of dichlorocarbene and its application to organic reactions: the catalytic action of octopus - type calix[6]arene, Bull. Chem. Soc. Jpn. 67 (1994) 792-799.
15. M. Rahinovitz, Y. Cohen, M. Halpern, Hydroxide initiated reactions under phase transfer catalysis conditions: mechanism and implications, Angew. Chem., Int. Ed. Engl. 25 (1986) 960-970.
16. M.-L. Wang, Y.-M. Hsieh, Dynamics of the reaction of 2,4,6-tribromo-phenol and benzyl bromide by phase transfer catalysis, J. Chem. Eng. Jpn. 66 (1993) 2149-2155.
17. J.P. Jayachandran, M.-L. Wang, Cycloalkylation of phenylacetonitrile with 1,4-dibromobutane catalyzed by aqueous sodium hydroxide and a new phase transfer reagent, Dq-Br, Appl. Catal. A: Gen. 198 (2000) 127-137.