4750-17-8

Usage

Physical state

Colorless liquid

Odor

Pungent

Uses

Building block in the synthesis of pharmaceuticals, agrochemicals, and fragrances

Applications

Production of dyes, coatings, and other specialty chemicals

Role in organic synthesis

Versatile intermediate

Reactions

Ability to undergo various reactions to produce a wide range of derivatives

Precursor

In the synthesis of cyclic compounds and complex organic molecules

Safety precautions

May cause skin and eye irritation

Storage and usage

Should be stored and used in a well-ventilated area

Upstream product

• 498-66-8 norbornene 
• 7732-18-5 water 
• 201230-82-2 carbon monoxide 
• 542-92-7 cyclopenta-1,3-diene 

Relevant academic research and scientific papers

First rhodium-catalyzed hydroformylation of cyclopentadiene

This paper describes the first rhodium-catalyzed hydroformylation of cyclopentadiene (Cpd) using a homogeneous catalyst system consisting of [Rh(OAc)2]2 and the chelate ligand BISBI. At a reaction temperature of 100°C and a syngas pressure of 30 bar the cyclopentane carbaldehyde is formed in 68% yield while 20% of the respective dialdehyde species are obtained within 3 hours. An important side reaction in Cpd hydroformylation reaction can be the dimerization of Cpd to its dimer dicyclopentadiene (Dcpd). This unwanted side reaction could be overcome by the use of tertiary alkyl amines as additives. Furthermore, the possibility to steer the reaction via the influence of the bite angle of diphosphine ligands was found.

Structural, Theoretical and Spectroscopic Characterisation of a Series of Novel Gold(I)-Norbornene Complexes Supported by Phenanthrolines: Effects of the Supporting Ligand

A series of novel gold(I) alkene complexes of general formula [Au(N^N)(η2-nb)][PF6] [N^N = PHEN (1,10-phenanthroline), NCP (2,9-dimethyl-1,10-phenanthroline), 4,7-DMP (4,7-dimethyl-1,10-phenanthroline), TMP (3,4,7,8-tetramethyl-1,10-phenanthroline), BTP (4,7-diphenyl-1,10-phenanthroline) and BTC (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline); nb = norbornene] were synthesized by a novel synthetic pathway. The novel cationic gold(I)-norbornene complexes were fully characterized by 1H and 13C NMR spectroscopy and the crystal structure of three complexes was solved by single-crystal X-ray diffraction. The correlations between the nature and position of the substituents on the ancillary ligand and the spectroscopic and structural data highlight variations on the nature of the bonding. The combination of experimental and DFT data allowed to evaluate the extent of σ-donation and π back-donation in the bond with the olefin, suggesting that a fine interplay between electronic and steric effects on the ancillary ligand can affect the bond properties and structural features of the complexes.

Catalytic Epoxidation of Alkenes by Co-orinatively Unsaturated Phosphino Complexes of Ruthenium(II) and Osmium(II)

Ruthenium(II) and osmium(II) complexes Y, where LL is 1,3-bis(diphenylphosphino)propane or 1-diphenylphosphino-2-(2'-pyridyl)ethane, promote the oxidation of a number of alkenes by PhIO, hypochlorites, and H2O2.