Phosphorus heterocycles, literature reviews

This chapter describes phosphorus heterocycles with greater than six-membered rings, which appeared in the literature after 1995. For the phosphorus macrocycles published before 1996, see reviews by Pabel and Wild in CHEC-II(1996) < 1996CHEC-II(9)947> and by Caminade and Majoral <1994CRV1183>. 

This chapter on the chemistry of heterocycles with two nonadjacent heteroatoms with at least one phosphorus, arsenic, or antimony , is an update to the earlier review in CHEC-II(1996) <1996CHEC-II(3)714>. It has been assembled by the Volume Editor at a late stage in the absence of a contribution from the originally commissioned author. As a consequence, there has been insufficient time for as thorough an assessment of the available literature, as would have been desirable. There has not been time to assemble detailed tables of data. Additionally, the subdivisions in this chapter do not follow completely the pattern in the rest of this volume, partly because of the short timescale and partly because this group of heterocycles does not lend itself fully to those subdivisions. However, it is the belief that all the most important information in the decade since 1995 has been summarized, and leading references to spectroscopic and X-ray data have been cited, but apologies are offered to any workers in this field whose contributions may not have been properly included or as fully described as they merit. 

Since three-membered rings with two heteroatoms including phosphorus to bismuth were not treated in the first edition of Comprehensive Heterocyclic Chemistry (CHEC-I) we have attempted, in this review, to comprehensively cover the literature up until the middle of 1994, including several reviews already written on three-membered heterocycles (90CRV997,92CRV1839). Taking into account the various synthetic routes, and the different strategies for the stabilization of these strained three-membered heterocycles, we have attempted to divide them into several series. 

The only comprehensive and readily-available surveys of thio- and seleno-phosphonic and -phosphinic acids appear to be those in the compilation by Kosolapoff and Maier which appeared during the 1970s, and those in the Houben-Weyl volumes. Some further information relevant to heterocyclic systems which possess endo- or exo-cyclic phosphorus-sulphur bonds has been surveyed by Mann Gefter has also provided a useful compilation of syntheses and data for unsaturated thiophosphonates and related compounds. As in the preceding chapters concerned with the synthesis of the various classes of phosphonic and phosphinic acids, literature surveys have been presented for individual compounds and the field, as a whole, is surveyed annually". In addition. Hall and Inch reviewed the mechanistic implications of changes in stereochemistry following displacement reactions at phosphorus in cyclic phosphorus(V) esters and amides, and in so doing discussed the reaction s of many such thiophosphoryl compounds. 

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