Butyltriphenylphosphonium

The oxidative potency of dichromates and chlorochromates decreases under less acidic conditions. This is so, for example, when a less acidic ammonium salt is included as counter-ion of a dichromate or chlorochromate anion. Thus, a number of ammonium dichromates and chlorochromates possessing a milder oxidative potency has been described with the specific purpose of allowing very selective oxidations of unsaturated alcohols in the presence of saturated ones. These selective dichromates and chlorochromates include bis(benzyltriethylammonium)dichromate,135 tetramethylethy-lenediammonium dichromate (TMEDADC),136 imidazolium dichromate (IDC),137 N, A -dimeth y I a m i n o py r id i n i u m chlorochromate (DMAPCC),138 l-(benzoylamino)-3-methylimidazolium chlorochromate (BAMICC)139 and butyltriphenylphosphonium chlorochromate (BTPPCC).140... 

A second-order dependence on both the reductant and acidity was observed in the oxidation of alcohols with butyltriphenylphosphonium dichromate study of MeCD2OH and Me2CDOH indicated the presence of a substantial kinetic isotope effect. The reaction was studied in 19 organic solvents and the rates were correlated with mul-tiparametric equations. The reaction is susceptible to both electronic and steric effects of the substituents. A mechanism involving the formation of a dichromate ester and an a-C-H cleavage has been proposed.4... 

Some other reaction courses were also seen. For example, 3a, R=octyl with butyllithium gave no significant yield of dodecane. The 31P chemical shift of an important component suggested an ylide, perhaps derived from butyltriphenylphosphonium from attack at P rather than C. Ethyl magnesium bromide with 3a, R=octyl gave mostly 1-bromooctane, but with butylmagnesium chloride, about 20% yield of dodecane was observed with no 1-chlorooctane. 

Chloroperbenzoic acid Sodium hydroxide Sodium metaperiodate Sodium bicarbonate n-Butyltriphenylphosphonium bromide Hydrogen peroxide Sodiumbis(trimethylsilyl)amide 2,4-Bis(trifluoromethyl)benzyltriphenyl-... 

McCarthy, J. E. G., Ferguson, S. J., and Kell, D. B., Estimation with an ion selective electrode of the membrane potential in cells of Paracoccus denitr icans from the uptake of the butyltriphenylphosphonium cation during aerobic and anaerobic respiration. Biochem. J. 196, 311-321 (1981). 

A number of redox reactions with benzimidazolium fluorochromate (BIFC), bipyridinium chlorochromate (BPCC), butyltriphenylphosphonium dichromate... 

Hajipour, A. R. Mallakpour, S. E. Malakoutikhah, M. Efficient and highly selective oxidation of primary and secondary alcohols by butyltriphenylphosphonium chlorochromate under non-aqueous conditions. Indian J. Chem., Sect. B 2003, 42B, 195-198. 

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