Antimony heterocyclic compounds

Phosphorus Heterocycles (Including some Arsenic and Antimony Heterocycles). M. J. Gallgher in W. L. F. Armarego, Stereochemistry of Heterocyclic Compounds, Part II, p. 339, Wiley, 1977. 

Other useful organometallic reagents for the preparation of tertiary stibines or related heterocyclic compounds are compounds of lithium, aluminum, tin, copper, zirconium, and other metals. " In most cases, these metal compounds are reacted with antimony chlorides or bromides. Good yields of tertiary stibines were, however, also obtained by the interaction (equation 3) of triaUcylaluminium reagents and tris(dimethylamino)stibine. ... 

A125. F. G. Mann, Chemistry of Heterocyclic Compounds, Vol. 1 Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony and Bismuth, 2nd ed. Wiley (Interscience), New York, 1970. A much shorter first edition was published in 1950. A126. C. A. McAuliffe, ed., Transition Metal Complexes of Phosphorus, Arsenic and Antimony ligands. Macmillan, New York, 1973. 

Six-Membered Heterocyclic Compounds with a Single Nitrogen Atom in the Ring to which are Fused Two or More Carbocyclic Ring Systems, and Six-Membered Ring Compounds where the Hetero-Atom is Phosphorus, Arsenic, Antimony or Bismuth. Alkaloids Containing a Six-Membered Heterocyclic Ring System... 

F. G. Mann, Heterocyclic Compounds of Phosphorus, Arsenic, Antimony, and Bismuth, Wiley-Interscience, New York, 1970. 

Majority of known perfluoroalkylated aromatic heterocyclic compounds contain one or several nitrogen atom(s) in the aromatic ring. Examples of fluoroalkylated aromatic six-membered heterocycles containing atoms, such as phosphorous or antimony are extremely rare and this is the reason why this chapter is mostly limited to preparation and chemical transformations of nitrogen-cotitammg aromatic heterocycles, providing limited number of references to only few known examples of trifluoromethyl s-1,3,5,2,4,6-triazatriphosphinines. 

Compounds with triple bonds, i.e. acetylenic compounds, continue to receive attention. Patents have been filed for mixtures of propargyl alcohol with, for example, cellosolve + a phenol formaldehyde resin + tar bases heterocyclic nitrogen compounds + acetylenic + dialkylthiourea or a quaternary + antimony oxide . 

There are many organometallic compounds of arsenic, antimony, and bismuth known that constitute series having chemical properties that differ markedly. These compounds generally decrease in stability in the order As > Sb > Bi, which agrees with the increasing difference in size of the atoms and carbon atoms. Arsenic compounds include both aliphatic derivatives and heterocycles such as arsabenzene,... 

The complex of tartaric acid and antimony (emetic) was described three centuries ago. Nevertheless, the structure of this compound has been elucidated these last fifteen years by X-ray diffraction ( 1 ). In fact, emetic presents a binuclear cyclic structure. Many authors mentioned similar complex with transition metals (vanadium (2), chromium (3)) or metalloids (arsenic (4), bismuth (5)). Emetic with phosphorus was not mentioned. Nevertheless, tartaric acid or alkyl tartrates has been utilized in phosphorus chemistry tartaric acid reacts with trialkyl phosphites giving heterocyclic phosphites (6). Starting from alkyl tartrates, we prepared spirophosphoranes with a P-H bond and sixco-ordinated compounds (7). With unprotected tartaric acid, many possibilities appear condensation as a diol, as a di(oc-hydro-xyacid), or even as a 8-hydroxyacid. 

Here again a note on nomenclature is needed. If compounds of type 25 are considered as substituted phosphoranes, names such as the one given above are appropriate. If, on the other hand, their heterocyclic nature stays in the foreground, the correct names (as used by Chemical Abstracts) are such as 5-phenyl-5,5 -spirobi[5H-dibenzophosphole]. Both naming procedures are consistent with IUPAC rules and are applicable to similar arsenic, antimony- and bismuth-heterocycles as well (see later chapters). 

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