HPLC of Formula: 97739-46-3. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane, is researched, Molecular C16H21O3P, CAS is 97739-46-3, about Phenylphosphatrioxa-adamantanes: bulky, robust, electron-poor ligands that give very efficient rhodium(I) hydroformylation catalysts. Author is Baber, R. Angharad; Clarke, Matthew L.; Heslop, Katie M.; Marr, Andrew C.; Orpen, A. Guy; Pringle, Paul G.; Ward, Andrew; Zambrano-Williams, Damaris E..
The cage phosphines 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (1a) and 1,3,5,7-tetraethyl-6-phenyl-2,4,8,trioxa-6-phosphaadamantane (1b) were made by the acid catalyzed addition of PhPH2 to the appropriate β-diketones; the acid used (HCl, H3PO4 or H2SO4) and its concentration affect the rate and selectivity of these condensation reactions. Phosphines 1a and 1b react with [PdCl2(NCPh)2] to form trans-[PdCl2(1a)2] (2a) and trans-[PdCl2(1b)2] (2b) as mixtures of rac and meso diastereoisomers. The Pt(II) chem. is more complicated and when 1a or 1b is added to [PtCl2(cod)], equilibrium mixtures of trans-[PtCl2L2] and [Pt2Cl4L2] (L = 1a or 1b) are formed in CH2Cl2 solution Meso/rac mixtures of trans-[MCl(CO)(1a)2] M = Ir (6a) or Rh (7a) are formed upon treatment of MCl3·nH2O with an excess of 1a and the anionic Co complex [NHEt3][CoCl3(1a)] (9) was isolated from the product formed by CoCl2·6H2O and 1a. The νCO values from the IR spectra of 6a and 7a suggest that 1a resembles a phosphonite in its bonding to Rh and Ir. Crystal structures of meso-2a, meso-2b, rac-6a and 9 are reported and in each case a small intracage C-P-C angle of ∼94° is observed and this may partly explain the bonding characteristics of ligands 1a and 1b. The cone angles for 1a and 1b are similar and large (∼200°). Rh complexes of ligands 1a and 1b are hydroformylation catalysts with similarly high activity to catalysts derived from phosphites. The catalysts derived from 1a and 1b gave unusually low linear selectivity in the hydroformylation of hexenes. This feature was further exploited in quaternary-selective hydroformylations of unsaturated esters; catalysts derived from 1a give better yields and regioselectivities than any previously reported catalyst.
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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics