131266-79-0Relevant academic research and scientific papers
Novel catalysts useful for catalyzing the coupling of arylhalides with arylboronic acids
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Page/Page column 5-6, (2008/06/13)
The present invention relates to a new method of cross-coupling aryl moieties comprising reacting an arylhalide with an arylboronic acid in the presence of a palladium compound and a compound comprising a di-alkylphosphine moiety.
The reaction of secondary phosphines and di-1-adamantylphosphine oxide with trifluoroacetic anhydride and hexafluoroacetone
Goerlich, Jens R.,Plack, Volker,Schmutzler, Reinhard
, p. 29 - 35 (2007/10/03)
While the secondary phosphines (1-Ad)2PH (1) (1-Ad=adamantyl) and Trt(Ph)PH (2) (Trt=triphenylmethyl) reacted readily with trifluoroacetic anhydride (TFAA) to give the trifluoroacetylphosphines 7 and 8. (1-Ad)2P(:O)H (6) could not be converted into the corresponding trifluoroacetylphosphine oxide 10 by treatment with TFAA. Compound 10 was observed by 19F and 31P NMR spectroscopy in the reaction of (1-Ad)2PC(:O)CF3 (7) with (H2N)2C(:O)·H2O2. Two pathways were observed for the reaction of 1 with excess hexafluoroacetone (HFA), starting from the primary HFA adduct (1-Ad)2PC(CF3)2OH (13). Oxidation of 13 led to the tertiary phosphine oxide 14 which was also available from (1-Ad)2P(:O)H (6) and HFA. Isomerization of 13 gave (1-Ad)2POCH(CF3)2 (15) whose oxidation with excess HFA furnished the phosphorane 16. Hydrolysis of 16 led to the phosphinic ester 17. As is known for Ph2PH (3), Ph(C6F5)PH (4) reacted with HFA to give the α-hydroxyphosphine 19. No reaction was observed when Trt(Ph)PH (2) and (C6F5)2PH (5) were treated with HFA.
ORGANOPHOSPHORUS COMPOUNDS WITH TERTIARY ALKYL SUBSTITUENTS. VI: A CONVENIENT METHOD FOR THE PREPARATION OF DI-1-ADAMANTYLPHOSPHINE AND DI-1-ADAMANTYLCHLOROPHOSPHINE
Goerlich, Jens R.,Schmutzler, Reinhard
, p. 211 - 216 (2007/10/02)
Di-1-adamantylchlorophosphine 3 is obtained by a three step sequence from commercially available adamantane.Despite the bulky 1-adamantyl groups at the phosphorus atom, it reacts readily with water to give di-1-adamantylphosphine oxide 4.Key words: 1-Adamantyl phosphorus compounds, Friedel-Crafts reaction, H/D-exchange, NMR.
Organophosphorus Compounds with Tertiary Alkyl Substituents. III: Synthesis and Reactions of Di-1-adamantyl-Substituted Phosphorus Compounds; Crystal Structure of Di-1-adamantylphosphinic Chloride
Goerlich, Jens R.,Fischer, Axel,Jones, Peter G.,Schmutzler, Reinhard
, p. 801 - 811 (2007/10/02)
The reaction of adamantane with PCl3/AlCl3, followed by hydrolysis, gave (1-Ad)2P(:O)Cl 1, which was converted to (1-Ad)2P(:O)F 2 and (1-Ad)2P(:S)Cl 3 by standard procedures.The structure of 1 was confirmed by a single crystal X-ray structure determinatio
DI-1-ADAMANTYLPHOSPHIN, EIN SRERISCH HOCH GEHINDERTES SEKUNDAERES PHOSPHIN. DARSTELLUNG UND REAKTIONEN
Goerlich, Jens R.,Schmutzler, Reinhard
, p. 141 - 148 (2007/10/02)
Di-1-adamantylphosphine 1 was synthesized by reduction of (1-Ad)2P(:O)Cl with LiAlH4 or HSiCl3.The reaction of 1 with H2O2, elemental sulfur and selenium afforded the corresponding secondary phosphine oxides, sulfides and selenides, (1-Ad)2P(:X)H (X = O, S, Se).In the reaction of 1 with two equivalents of Me3SiN3 oxidation occured with formation of (1-Ad)2P(:NSiMe3)NHSiMe3 6.Despite the steric hindrance, MeI quaternized the P-atom in 1 to give I 7.The phosphine (1-Ad)2PMe 8 was formed in the reaction of 7 with NEt3 and was oxidized by O2 to give (1-Ad)2P(:O)-Me 9.Key words: Di-1-adamantylphosphine; Di-1-adamantylphosphine oxide, sulfide, selenide, NMR.
