62672-77-9Relevant articles and documents
β-TRICHLOROTELLURO KETONES. PREPARATION AND EXTREMELY FACILE DEHYDROTELLURATION LEADING TO α-METHYLENE KETONES
Nakahira, Hiroyuki,Ryu, Ilhyong,Han, Libiao,Kambe, Nobuaki,Sonoda, Noboru
, p. 229 - 232 (1991)
β-Trichlorotelluro ketones 4 generated in situ from siloxycyclopropanes 1 and TeCl4 react with dimethyl sulfoxide or some amines under mild conditions to provide the corresponding α-methylene ketones 3 in good yields.
β-Trichlorostannyl Ketones and Aldehydes. Preparation and Facile Amine-Induced Dehydrostannation Leading to α-Methylene Ketones and Aldehydes
Nakahira, Hiroyuki,Ryu, Ilhyong,Ikebe, Masanobu,Oku, Yoshiaki,Ogawa, Akiya,et al.
, p. 17 - 28 (2007/10/02)
Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give β-trichlorostannyl ketones and aldehydes 3 in high yields.The β-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding α-methylene ketones and aldehydes 4.The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N',N',-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclooctane (DABCO), and the yields are good to high.One-pot conversion from siloxycyclopropanes 1 to α-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful.The 1H NMR, 13C NMR, 119Sn NMR, and IR spectral properties of β-stannyl ketones and aldehydes are also reported.
Silicon-Directed Nazarov Reactions II. Preparation and Cyclization of β-Silyl-substituted Divinyl Ketones
Jones, Todd K.,Denmark, Scott E.
, p. 2377 - 2396 (2007/10/02)
Two general methods for the preparation of β-silyl-substituted divinyl ketones have been developed starting from either α,β-unsaturated aldehydes or simple ketones.Anhydrous FeCl3 induces the cyclization to cyclopentenones under mild conditions and in good yields with predictable and complete control over the position of the double bond in the five-membered ring.The observed effects of substituents on rate can be explained by a rate-determining cationic electrocyclization.Silyl substitution has been shown to retard the reaction.