Ozonolysis of vinylsilanes
Ozonolysis of vinylsilanes
复制标题
乙烯基硅烷的臭氧分解
DOI：
10.1021/ja00469a056
复制
发表时间：
1978
影响因子：
15
通讯作者：
H. Wuest
中科院分区：
文献类型：
--
作者：
G. Buechi;H. Wuest
C6H13C= CSi (CH3) 3 c6hI3cooch3 54 ref 12 c4h13cocooch3 30 a03, 9: 1 CH30H-CH2C12,-20 C;(CH3) 2S, 3 h, 20 C. b03, EtOH,-15 C, NaBH4. cQ3, 9: 1 CH30H-CH2C12,-20 C; H20, 24 h, 20 C. d03, 9: 1CH30H-CH2C12,-15 C;(CH3) 2S, HC-(OCH3) 3, p-TSA, 24 h, 20 C. e Also formed in low yields were 2-hydroxy cyclohexanone, 6-oxoadipic acid, and adipic acid mono-methyl ester.Ozonolysis, discovered as early as 1855, remains one of the most efficient and economical methods to cleave carbon-carbon multiple bonds. 1 It appeared to be suitable for the degradation of vinylsilane l2 to the norketone 3, 3 but ozonization in methanol followed by hydrolytic decomposition of intermediates afforded 67%-hydroperoxy aldehyde 4 and only 18% anticipated ketone 3 (Scheme I). Reductive workup after ozonization gave mainly the-hydroxy aldehyde 2 and again onlyminor amounts of the ketone 3. In carbon tetra-chloride ozonolysis of 1 produced some formic acid trimethylsilyl ester (6), an equivalent amount of ketone 3, and an unstable substance that was not isolated in pure form. Tenta-
