Reineckate

M. G. Reinecke, Tetrahedron 38, 427 (1982) R. Mumgan, Meta/Zation, Conformationa/Ana/ysis, Hydrogen Exchange and Rearrangement in Amides, Doctoral thesis. University of Plorida, Gainesville, 1987 A. Weissberger and E. C. Taylor, eds.. The Chemistry of Heteroyc/ic Compounds, in Ref. 11, pp. 448—449. 

Choline reineckate is used in the spectrophotometric determination of choline. Ammonium reineckate [13573-16-5] forms a water-insoluble complex with choline. The complex is soluble in acetone and a widely used method for determination of choline is by light absorption of acetone solutions... 

Ammonium reineckate (Reineckate salt) [13573-16-5] M 345.5, m 270-273 (dec). Crystd from water, between 30° and 0°, working by artificial light. Solns of reineckate decompose slowly at room temperature in the dark and more rapidly at higher temperatures or in diffuse sunlight. 

Potassium reineckate [34430-73-4] M 357.5. Crystd from KNO3 soln, then from warm water [Adamson J Am Chem 5oc 80 3183 1958]. 

The process of isolation finally adopted by the former authors consists in precipitating as reineckates the water-soluble bases contained in a methyl alcoholic extract of the curare. The mixed reineckates are further purified, by solution in acetone and precipitation with water as often as may be necessary. The product so cleaned represents the bulk of the biological activity of the crude drug the mother liquors may contain curine (p. 374), which indicates a menisperm as one of the components of such curares. The mixed reineckates are then fractionated chromato-graphically over alumina and the components isolated as chlorides by the use of silver sulphate and barium chloride in succession. This process has been modified in detail by Schmid and Karrer, who have also found that with their curare, the more soluble reineckate fraction includes less potent quaternary alkaloids. 

The total crude alkaloid from tlie soluble reineckate fraction had the low curarising potency 25 mgm./kilo frog. It consisted mainly of quaternary alkaloids and nothing crystalline lias so far been obtained from the non-quaternary portion. 

Many alkaloids are obtained in such small quantities that it is not possible to describe them in detail, and recourse must be had to giving characteristics for picrates, aurichlorides and similar compounds. The reineckates, first used by Christensen and later by Rosenthaler, are a useful addition to such compounds, and have been so used recently by Evans and Partridge for the characterisation of solanaceous alkaloids. 

It is noteworthy that only in the case of dehydroquinolizidine derivatives does monomethylation produce the N-alkylated product. The formation of dialkylated products can be explained by a disproportionation reaction of the monoalkylated immonium salt caused by either the basicity of the starting enamine or some base added to the reaction mixture (most often potassium carbonate) and subsequent alkylation of the monoalkylated enamine. Reinecke and Kray 113) try to explain the different behavior of zJ -dehydroquinolizidine and zJ -dehydroquinolizidine derivatives by the difference in energies of N- and C-alkylation transition states because of the presence of I strain. 

The hospitality of the Department of Chemistry and Professor James P. Kutney at the University of British Columbia, Vancouver, Canada, during the time of writing this chapter is highly appreciated. 1 am indebted to the secretarial staff of the Department, Ms. Carolyn Delheij-Joyce in particular, for their extensive and patient input in the typing and production, and to Professor Manfred Reinecke for his help and useful suggestions. 

Cardaminol (Reinecke)-comb. wfm Cardiazol (Knoll) wfm Indo vert (Do lorgiet)-comb. wfm... 

Rey C, Reinecke HJ, Besser R (1984) Methyltin intoxication in six men Toxicologic and clinical aspects. Veterinary and Human Toxicology, 26 121-122. 

Originally, compounds containing coordination complexes were given common names such as Prussian blue (KFe[Fe (CN)g ]), which is deep blue, or Reinecke s salt (NH4[Cr (NH3)2 (NCS)4]), named for its first maker. Eventually, coordination compounds became too numerous for chemists to keep track of all the common names. To solve the nomenclature problem, the International Union of Pure and Applied Chemistry (lUPAC) created a systematic procedure for naming coordination compounds. The following guidelines are used to determine the name of a coordination compound from its formula, or vice versa ... 

Reinecke W, DJ Jeenes, PA Williams, H-J Knackmuss (1982) TOL plasmid pWWO in constrncted halobenzoatedegrading Pseudomonas strains prevention of meta pathway. / SacterioZ 150 195-201. 

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