scholarly journals Convenient Synthesis of β-Silyl Ketones from β-Stannyl Enol Silyl Ethers via a [1,4] Anionic Rearrangement of Silicon

1990 ◽  
Vol 63 (11) ◽  
pp. 3361-3363 ◽  
Author(s):  
Hiroyuki Nakahira ◽  
Ilhyong Ryu ◽  
Akiya Ogawa ◽  
Nobuaki Kambe ◽  
Noboru Sonoda
Keyword(s):  
Silyl Ethers ◽  
Convenient Synthesis ◽  
Enol Silyl Ethers

ChemInform Abstract: Convenient Synthesis of β-Silyl Ketones from β-Stannyl Enol Silyl Ethers via a (1,4) Anionic Rearrangement of Silicon.

ChemInform ◽  
2010 ◽  
Vol 22 (14) ◽  
pp. no-no
Author(s):  
H. NAKAHIRA ◽  
I. RYU ◽  
A. OGAWA ◽  
N. KAMBE ◽  
N. SONODA
Keyword(s):  
Silyl Ethers ◽  
Convenient Synthesis ◽  
Enol Silyl Ethers

Thermal rearrangement of functionalized 1,2-divinylcyclopropane systems. A convenient synthesis of substituted 4-cyclohepten-1-ones

1986 ◽  
Vol 64 (1) ◽  
pp. 180-187 ◽  
Author(s):  
Edward Piers ◽  
Max S. Burmeister ◽  
Hans-Ulrich Reissig
Keyword(s):  
Acid Hydrolysis ◽  
The Other ◽  
Thermal Rearrangement ◽  
Enol Ethers ◽  
Acyl Chlorides ◽  
Silyl Ethers ◽  
Convenient Synthesis ◽  
Enol Silyl Ethers ◽  
Hydrolysis Of ◽  
Subsequent Acid

Reaction of the acyl chlorides 14–21 with lithium (phenylthio)(cis-2-vinylcyclopropyl)cuprate (2) provided the ketones 22–29. Compounds 22–25, upon treatment with i-Pr2NLi-Me3SiCl, were converted cleanly into the enol silyl ethers 30–33, which gave the 1,4-cycloheptadienes 34–37 upon thermolysis (100–110 °C). Acid hydrolysis of the latter materials produced the corresponding 4-cyclohepten-1-ones 38–41. However, subjection of the cis-2-vinylcyclopropyl ketones 26–29 to i-Pr2NLi-t-BuMe2SiCl afforded, in each case, a mixture of isomeric enol ethers (26 → 42 + 44 (1:1); 27 → 43 + 45 (1:9); 28 → 56 + 58 (1:1); 29 → 57 + 59 (4:1)). Thermolysis (150–175 °C) of these mixtures, followed by acid hydrolysis of the resultant products, gave the 4-cyclohepten-1-ones 54, 55, 64, and 65, admixed with the corresponding 3-methylenecyclopentenes 52, 53, 62, and 63. On the other hand, treatment of the trans-2-vinylcyclopropyl ketones 70–74 with i-Pr2NLi–t-BuMe2SiCl provided exclusively or predominantly the enol ethers 75–79. Thermolysis (230 °C) of the latter materials and subsequent acid hydrolysis of the resultant products 80, 50, 51, 60, and 61 afforded the 4-cyclopenten-1-ones 38, 54, 55, 64, and 65.

A convenient synthesis of 2,2-difluoro enol silyl ethers from chlorodifluoromethyl ketones

1983 ◽  
Vol 24 (5) ◽  
pp. 507-510 ◽  
Author(s):  
Masayuki Yamana ◽  
Takashi Ishihara ◽  
Teiichi Ando
Keyword(s):  
Silyl Ethers ◽  
Convenient Synthesis ◽  
Enol Silyl Ethers

A Convenient Synthesis of α-Phenylseleno Ketones and Aldehydes from Enol Silyl Ethers and Phenylselenenyl Bromide

Synthesis ◽  
1977 ◽  
Vol 1977 (12) ◽  
pp. 874-876 ◽  
Author(s):  
Ilhyong RYU ◽  
Shinji MURAI ◽  
Isamu NIWA ◽  
Noboru SONODA
Keyword(s):  
Silyl Ethers ◽  
Convenient Synthesis ◽  
Enol Silyl Ethers
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