Bismuth heterocyclic compounds

Synthesis of Heterocycles Using Bismuth(III) Compounds as Catalysts. 48... 

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). 

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. 

Bismuth(III) compounds in syntheses and transformations of heterocycles 02T8373. 

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. 

Environmentally friendly organic synthesis (particularly, that of heterocycles) using bismuth(III) compounds as catalysts 12TCC(311)45. Heterocycle synthesis based on palladium-catalyzed C—H bond functionalization methods 12COC96. 

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. 

Inclusion of bismuth atoms in heterocyclic ring complexes has been actively investigated for a number of years. Complexes of the type (17), for example, l-phenyl-2,5-dimethylbismole, have been sought for comparison with pyrrole derivatives and for information about the degree of aromaticity in its heavier analogs. Compound (17) is prepared via the addition of 2(Z),5(Z)-dilithio-3,4-dimethylhexa-2,4-diene to PhBil2 in 28% yield. This heterocycle is converted to the dibismuthine in the standard fashion treatment of (17) with Na in liquid NH3 followed by addition of 1,2-dichloroethane. 

Distibanes and dibismuthanes in which the antimony or bismuth atoms are incorporated in five-membered heterocycles are named bistiboles and bibismoles. This important class of thermochromic compounds has been studied intensively by the group of Ashe. The synthesis and X-ray structure determination of tetramethylbistibole. 

Breunig, H. J. In Chemistry of Organic Arsenic, Antimony and Bismuth Compounds Patai, S. Ed. Wiley New York, 1994 Chapter 14, Organoarsenic and organoantimony heterocycles, pp 563-578. 

The heterocyclic 10,10-dichloro-10-(4-methylphenyl)phenothia-10X5-bismine-5,5-dioxide (48) is a relatively stable substance, which slowly decomposes at room temperature to afford the ligand coupling product, 4-chlorotoluene. However, treatment of this bismuth compound with the sodium salt of dibenzoylmethane resulted only in the transfer of the tolyl group. The monoaryl derivative (49) and the bismuth containing fragment (50) were recovered in good yields (76% and 74% respectively). ... 

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