BETA-TRICHLOROSTANNYL KETONES AND ALDEHYDES - PREPARATION AND FACILE AMINE-INDUCED DEHYDROSTANNATION LEADING TO ALPHA-METHYLENE KETONES AND ALDEHYDES

被引：51

作者：

NAKAHIRA, H ^{[1
]}

RYU, I ^{[1
]}

IKEBE, M ^{[1
]}

OKU, Y ^{[1
]}

OGAWA, A ^{[1
]}

KAMBE, N ^{[1
]}

SONODA, N ^{[1
]}

MURAI, S ^{[1
]}

机构：

[1] OSAKA UNIV,FAC ENGN,DEPT APPL CHEM,SUITA,OSAKA 565,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 01期

关键词：

D O I：

10.1021/jo00027a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give beta-trichlorostannyl ketones and aldehydes 3 in high yields. The beta-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding alpha-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-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to alpha-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The H-1 NMR, C-13 NMR, Sn-119 NMR, and IR spectral properties of beta-stannyl ketones and aldehydes are also reported.

引用

页码：17 / 28

页数：12