137518-35-5Relevant academic research and scientific papers
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.
