Production of high purity alkali metal diarylphosphide and cyclo

Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus containing

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

568 8, C07F 950

Patent

active

058667202

ABSTRACT:
(1) Alkali metal diarylphosphides are formed by mixing triarylphosphine with, and preferably introducing triarylphosphine into, a two-phase mixture one or more alkali metals, preferably a mixture or alloy of sodium and potassium, in an anhydrous organic liquid diluent in the presence of molecular hydrogen. (2) To form a cycloalkyldiarylphosphine, at least a portion of the reaction mixture formed as in (1) (or alkali metal diarylphosphide recovered therefrom) and cycloalkyl mesylate or tosylate are mixed together and maintained under suitable reaction conditions. Reaction (2) is driven by the presence of residual sodium from reaction (1). Conduct of reaction (2) under a hydrogen atmosphere suppresses undesirable side reactions.

REFERENCES:
patent: 3775482 (1973-11-01), Hewertson
patent: 4618720 (1986-10-01), Bay et al.
patent: 4668823 (1987-05-01), Murray
patent: 5288912 (1994-02-01), Devon
patent: 5354894 (1994-10-01), Devon
patent: 5654485 (1997-08-01), Senaratne
patent: 5710340 (1998-01-01), Senaratne
Aguiar et al., "Lithium Diphenylphosphide: A Convenient Source and Some Reactions", JOC Mar. 1962, vol. 27, pp. 1001-1004.
Toth et al., "Aspects of the Cleavage of Phosphines with Potassium: Synthesis and Reactivity of Lithium and Potassium Bis(p-(dimethylamino)phenyl)phosphide", Organometallics 1990, vol. 9, No. 3, pp. 675-680.
Rossi et al., "Reaction of l-Bromoadamantane with Diphenylphosphide and Dephenylarsenide Ions by the SRN1 Mechanism. Facile Nucleophilic Substitution at the Bridgehead Position", J Org Chem 1982, vol. 47, No. 24, pp. 4654-4657.
Aguiar et al., "The Reaction of Lithium Diphenylphosphide and Simple Aryl Halides", Aug. 1963, vol. 28, pp. 2091-2093.
Tsvetkov et al., "A Simple Synthesis and Some Synthetic Applications of Substituted Phosphide and Phosphinite Anions", Synthesis, Mar. 1986, pp. 198-208.
Hayashi et al., "Catalytic Asymmetric Hydroformylation by the Use of Rhodiumcomplexes of Chiral Bidentate Phosphorus Ligands Bearing Saturated Ring Skeletons", Sep. 1979, Bulletin of the Chemical Society of Japan, vol. 52, No. 9, pp. 2605-2608.
Morrison et al., "Synthesis of Menthyl-and Neomenthyldiphenylphosphine. Epimeric, Chiral, Tertiary Phosphine Ligands for Asymmetric Synthesis", J Org Chem, vol. 39, No. 2, 1974, pp. 270-272.
Wittenberg and Gilman, "Lithium Cleavages of Triphenyl Derivatives of Some Group Vb Elements in Tetrahydrofuran", J Org Chem vol. 23, pp. 1063-1065, Jul. 1958.
Kuchen and Buchwald, "Reactions of diphenylphosphine Sodium", Angew Chem 69, pp. 307-308 (1957) -Abstract Attached.
CA:119:250057 abs of "Reactions of cycloalkyl chlorides and bromides with diphenylphosphide ions in liquid ammonia" by Nazareno J Physl Org Chem 6(7), pp. 421-426, 1993.
CA:123:199005 abs of "A new efficient preparation of polyfunctional phosphines using zinc organometallicas", Tetrahedron Lett 36(26) pp. 4591-4594, 1995.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Production of high purity alkali metal diarylphosphide and cyclo does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Production of high purity alkali metal diarylphosphide and cyclo, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Production of high purity alkali metal diarylphosphide and cyclo will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1118763

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.