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2,3-Dihydrofuran is a versatile reagent used in lanthanide-catalyzed Diels-Alder reactions with 2-pyrones and in Rh(II)-stabilized cycloadditions with vinylcarbenoids. It is applied for alkylation by active methylene compounds, catalyzed by trans-Dichlorobis(triphenylphosphine)palladium(II). It is also used in the preparation of biologically active compounds such as antitumor agents.
Ulrike Kohlweyer, et al. Tetrahydrofuran degradation by a newly isolated culture of Pseudonocardia sp. strain K1.FEMS Microbiol. Lett.2000,186301-306.
Fumiyuki Ozawa, et al. Catalytic asymmetric arylation of 2,3-dihydrofuran with aryl triflates.J. Am. Chem. Soc.,1991,113(4), 1417-1419.
For lithiation at the 5-position, see: Tetrahedron Lett., 4187 (1977); Org. Synth. Coll., 9, 530 (1998). For alkylation by active methylene compounds, catalyzed by trans-Dichlorobis(triphenylphosphine)palladium(II), 10491, see: J. Org. Chem., 47, 2812 (1982). For catalytic asymmetric arylation, see: J. Am. Chem. Soc., 113, 1417 (1991); Pure Appl. Chem., 64, 421 (1992).
Forms tetrahydrofuranyl esters (acyl hemiacetals) with carboxylic acids. These react with Grignard reagents to give good yields of ketones with minimal enolization or double addition (tertiary alcohol formation). The utility of other acyl hemiacetals as ketone precursors has also been studied: J. Org. Chem., 61, 6071 (1996):
Hazard Statements: H225-H302-H319
Highly flammable liquid and vapour. Harmful if swallowed. Causes serious eye irritation.
Precautionary Statements: P210-P280a-P240-P303+P361+P353-P305+P351+P338-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Dispose of contents/container in accordance with local/regional/national/international regulations.