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Sigma-Aldrich

(R)-(–)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane

96%

Synonym(s):

(R)-Phanephos

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About This Item

Empirical Formula (Hill Notation):
C40H34P2
CAS Number:
364732-88-7
Molecular Weight:
576.65
MDL number:
MFCD03094575
UNSPSC Code:
12352002
PubChem Substance ID:
24885681
NACRES:
NA.22

Assay

96%

form

solid

optical activity

[α]/D -34±4°, c = 1 in chloroform

mp

222-226 °C

InChI

1S/C40H34P2/c1-5-13-35(14-6-1)41(36-15-7-2-8-16-36)39-29-31-21-25-33(39)27-23-32-22-26-34(28-24-31)40(30-32)42(37-17-9-3-10-18-37)38-19-11-4-12-20-38/h1-22,25-26,29-30H,23-24,27-28H2

InChI key

GYZZZILPVUYAFJ-UHFFFAOYSA-N

Application

(R)-(-)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane may be used as a ligand in the following processes:
  • Enantioselective reductive cyclization of 1,6-enynes via asymmetric hydrogenation in the presence of a rhodium catalyst to form alkylidene-substituted heterocycles.
  • Asymmetric hydroboration of 3,3-disubstituted cyclopropenes to form 2,2-disubstituted cyclopropyl boronates.
  • Asymmetric ring-opening reactions of azabenzonorbornadienes in the presence of zinc(II) triflate and palladium(II) acetate to form aminodihydronaphthalenes.
Efficient ligand for asymmetric hydrogentation of dehydroamino acids, methyl esters and keytones.

Legal Information

Sold in collaboration with Johnson Matthey Catalyst for research purposes only. US5874629 and any patents arising therefrom apply.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Amide bond formation via C (sp 3)?H bond functionalization and CO insertion
Liu, Huizhen, et al.
Chemical Communications (Cambridge, England), 50.3, 341-343 (2014)
Catalytic enantioselective hydroboration of cyclopropenes.
Rubina M, et al.
Journal of the American Chemical Society, 125(24), 7198-7199 (2003)
Enantioselective Reductive Cyclization of 1, 6-Enynes via Rhodium-Catalyzed Asymmetric Hydrogenation: C- C Bond Formation Precedes Hydrogen Activation.
Jang HY, et al.
Journal of the American Chemical Society, 127(17), 6174-6175 (2005)
Highly efficient ruthenium-catalyzed oxime to amide rearrangement
Owston, Nathan A., Alexandra J. Parker, and Jonathan MJ Williams
Organic Letters, 9.18, 3599-3601 (2007)
[2.2] Paracyclophane Derivatives: Synthesis and Application in Catalysis
Paradies, Jan
Synthesis, 2011.23, 3749-3766 (2011)
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