Electroorganic chemistry. 124. Electroreductive intramolecular coupling of. alpha.-(. omega.-bromoalkyl). beta.-keto esters

T Shono, N Kise, N Uematsu, S Morimoto…

Index: Shono, Tatsuya; Kise, Naoki; Uematsu, Nobuyuki; Morimoto, Shinji; Okazaki, Eiichi Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 5037 - 5041

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Citation Number: 23

Abstract

Intramolecular coupling occurs when cyclic a-(bromomethyl)@-keto esters are electrochemically reduced in the presence of trimethylsilyl chloride and one-carbon ring- enlarged products are obtained in reasonable yields. Electroreduction of a-(7-bromopropyl) &keto esters also affords the corresponding five-membered cyclized products and/or the corresponding ring-opened compounds. The ease of ring opening of the cyclized products ...