[(1S,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl]diphenylphosphine

[43077-29-8] C22H29P (MW 324.44) InChI = 1S/C22H29P/c1-17(2)21-15-14-18(3)16-22(21)23(19-10-6-4-7-11-19)20-12-8-5-9-13-20/h4-13,17-18,21-22H,14-16H2,1-3H3/t18-,21+,22+/m1/s1 InChIKey = BEYDOEXXFGNVRZ-COPCDDAFSA-N Phosphine, [(1R,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl]diphenyl-, rel-[32511-22-1] InChI = 1S/C22H29P/c1-17(2)21-15-14-18(3)16-22(21)23(19-10-6-4-7-11-19)20-12-8-5-9-13-20/h4-13,17-18,21-22H,14-16H2,1-3H3/t18-,21+,22+/m0/s1 InChIKey = BEYDOEXXFGNVRZ-VLCRHTCISA-N Phosphine, [(1R,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl]diphenyl-[38053-73-5] InChI = 1S/C22H29P/c1-17(2)21-15-14-18(3)16-22(21)23(19-10-6-4-7-11-19)20-12-8-5-9-13-20/h4-13,17-18,21-22H,14-16H2,1-3H3/t18-,21+,22+/m0/s1 InChIKey = BEYDOEXXFGNVRZ-VLCRHTCISA-N Phosphine, [(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]diphenyl-[43077-31-2] InChI = 1S/C22H29P/c1-17(2)21-15-14-18(3)16-22(21)23(19-10-6-4-7-11-19)20-12-8-5-9-13-20/h4-13,17-18,21-22H,14-16H2,1-3H3/t18-,21+,22-/m1/s1 InChIKey = BEYDOEXXFGNVRZ-BVYCBKJFSA-N (chiral monodentate phosphine ligand for asymmetric catalysis, resolution of organometallic complexes) Alternative Names: (+)-(S)-NMDPP; (+)-NMDPP; (+)-neomenthyldiphenylphosphine; (S)-neomenthyldiphenylphosphine; diphenyl-(+)-neomenthylphosphine; neomenthyldiphenylphosphine; d-neomenthyldiphenylphosphine. Physical Data: mp 98–99 °C; white crystalline solid. Solubility: soluble in EtOAc, THF, DMI, benzene, DCM, and CHCl3; slightly soluble in MeOH and EtOH. Form Supplied in: only the dextrorotatory antipode, (+)-NMDPP, is commercially available in variable levels of purity. Analysis of Reagent Purity: NMDPP oxide is a tenacious impurity and is assayed by 31P NMR (300 MHz, THF) δ: 33 (NMDPP oxide), −14.9 (NMDPP). Preparative Methods: NMDPP is prepared by the formation of diphenylphosphide from diphenylphosphine,1 diphenylphosphinous chloride,2 or triphenylphosphine,3 followed by alkylation with menthyl chloride or mesylate. (−)-Menthyldiphenylphosphine ((−)-MDPP), an epimer of (+)-NMDPP at C-1 of the menthyl ring, is prepared similarly by the displacement of neomenthylchloride with diphenylphosphide1a or, alternatively, by the displacement of diphenylphosphinous chloride with the Grignard reagent derived from menthyl chloride.4 Purification: recrystallized from MeOH or EtOH at reflux (degassed with N2) with rigorous exclusion of oxygen. Handling, Storage, and Precautions: oxygen must be excluded to avoid formation of the phosphine oxide; reagent is stable for extended periods when stored in a glovebox.