64028-02-0Relevant articles and documents
Concise Syntheses of 3-Methylenetetrahydrofuran-2-one Derivatives and Related Systems
Adlington, Robert M.,Barrett, Anthony G. M.
, p. 2848 - 2863 (2007/10/02)
Using the Shapiro reaction, the title compounds were prepared in 'one pot' from the consideration of two ketones, or an aldehyde and a ketone, with carbon dioxide.For example, acetone 2,4,6-tri-isopropylbenzenesulphonylhydrazone was treated in sequence with n-butyl-lithium (-50 deg C), acetone (-50 deg C), n-butyl-lithium (-78 to 0 to -78 deg C), carbon dioxide (-78 deg C), and trifluoroacetic acid (25 deg C) to give 5,5-dimethyl-3-methylenetetrahydrofuran-2-one.The reaction was extended to prepare derivatives of 3-methylenetetrahydropyran-2-one and 3,5-dimethylenetetrahydrofuran-2-one.
The Conversion of Aldehydes and Ketones via their 2,4,6-Tri-isopropylbenzenesulphonyl Hydrazones into Nitriles containing One Additional Carbon Atom
Jiricny, Josef,Orere, Daniel M.,Reese, Colin B.
, p. 1487 - 1492 (2007/10/02)
2,4,6-Tri-isopropylbenzenesulphonyl hydrazones of aliphatic and alicyclic aldehydes and ketones react readily with potassium cyanide in boiling methanol solution to give the corresponding nitriles (containing one more carbon atom than the original aldehyde or ketone) in satisfactory yield. Under the same conditions, benzaldehyde 2,4,6-tri-isopropylbenzenesulphonyl hydrazone gives phenylacetonitrile in very low yield.In some cases, the arenesulphonyl hydrazones may be generated in situ, in methanol solution, from the carbonyl compounds and 2,4,6-tri-isopropylbenzenesulphonohydrazide (11a), thereby constituting a one-pot preparation or the nitriles.
