(E)- And (Z)-1-(Phenylsulfonyl)-4-(trimethylsilyl)-2-butenes: Synthetic Equivalents for the 1-(1,3-Butadienyl) Anion and the 1,1-(1,3-Butadienyl) Dianion

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4181-4192

  Meagher, Timothy P ^a   Yet, Larry ^a   Hsiao, Chi Nung ^a   Shechter, Harold ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001316464     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970545k     Document Type: Article

References (41)

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11. 2O or THF greatly affects the yield of 9 upon reaction with magnesium. When the (chloromethyl)trimethylsilane is ∼3.33 M, the yield of 9 is ∼95%. Under very dilute conditions, the yield of 9 is greatly lowered, (b) Phenylsulfenyl chloride should be added slowly so as to maintain the reaction temperature below -60°C. At higher temperatures side products are formed which reduce the yield and make purification of 12 difficult.
12. 2O or THF greatly affects the yield of 9 upon reaction with magnesium. When the (chloromethyl)trimethylsilane is ∼3.33 M, the yield of 9 is ∼95%. Under very dilute conditions, the yield of 9 is greatly lowered, (b) Phenylsulfenyl chloride should be added slowly so as to maintain the reaction temperature below -60°C. At higher temperatures side products are formed which reduce the yield and make purification of 12 difficult.
13. 2O or THF greatly affects the yield of 9 upon reaction with magnesium. When the (chloromethyl)trimethylsilane is ∼3.33 M, the yield of 9 is ∼95%. Under very dilute conditions, the yield of 9 is greatly lowered, (b) Phenylsulfenyl chloride should be added slowly so as to maintain the reaction temperature below -60°C. At higher temperatures side products are formed which reduce the yield and make purification of 12 difficult.
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