Selenium-containing phosphorus

Series of selenium-containing phosphorus compounds (137-139) have been reported by Kimura and Murai. Phosphinoselenoic amides 137 were prepared from racemic phosphinoselenoic chlorides (138) and chiral amines and the individual isomers could be separated by column chromatography in some cases.Reaction of 137 with tributylphosphine afforded the P(III) aminophosphines with retention of configuration at the phosphorus atom. (5)-methylbenzylamine was also used to prepare both enantiomers of phosphinoselenoic chlorides 138 in 96% ee. In contrast to the oxygen analogues, they were found to be stable and could be purified by column chromatography. Several compounds, such as 139 for example, were prepared by stereoselective nucleophilic substitutions of the Cl atom. ... 

Bansal et al. found that the recently synthesized phosphatriazolo[l,5- ]pyridines can undergo addition reaction on the phosphorus atom when treated with sulfur or selenium in the presence of a secondary amine <1995ZNB558> (Scheme 15). Thus, reaction of 4 with these reagents yields under mild conditions the sulfur- or selenium containing addition products 51a and 51b in fair yield. 

J. Susanne Becker, for joining me in a new and interesting cooperation on metal-, phosphorus-and selenium-containing proteins (metallo-, phospho- and selenoproteomics) using a combination of LA-ICP-MS and MALDI-MS. 

Yamazaki [51] has reviewed a number of stoichiometric cycloaddition reactions at the cobaltacyclopentadiene ring system that lead to a plethora of heterocycles. For example, five- and six-membered heterocycles containing nitrogen, sulfur, selenium, and phosphorus have been made accessible by this route (eq. (20)) [52]. The co-cyclization of substituted alkynes and isocyanates in the presence of a rhodium metallocycle gives 2-pyridones (eq. (21)) [53]. 

The (5,5)-fused bicyclic ring system with one fusion nitrogen atom and three additional heteroatoms in a 2 1 distribution over both live-membered rings (2N1) allows for a large variety of conceivable structures. The additional heteroatoms are mainly nitrogen, oxygen, and sulfur a few representatives of (5,5)-fused ring system also contain phosphorus, selenium or silicon atoms. 

A few examples of systems containing phosphorus, arsenic, or selenium in the five-membered ring were found. In view of space limitations, treatment has been restricted to the listing of a selection of relevant references. [l,3]Azaphospholo[l,2-a]pyridine (190 X = P) <87TLl5ll, 91CB475> ... 

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