The Journal of Organic Chemistry

. alpha.-Heterosubstituted phosphonate carbanions. 11. Benzoins via an acyl anion equivalent. Novel one-pot preparation of benzo [b] furans via benzoins using …

RE Koenigkramer, H Zimmer

Index: Koenigkramer, Rusty E.; Zimmer, Hans Journal of Organic Chemistry, 1980 , vol. 45, # 20 p. 3994 - 3998

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Citation Number: 42

Abstract

Discussion (A) Benzoins. Far the present studies (Scheme I) diethyl 1-(trimethylsi1oxy)-1- phenylmethanephosphonate (1) was prepared1'J8 in excellent yield (94%) in an Arbuzov- type reaction by refluxing a mixture of triethyl phosphite, chlorotriinethylsilane, and benzaldehyde evolving ethyl chloride as byproduct. At-60" C, the treatment of 1 with lithium diisopropylamide (LDA) in tetrahydrofuran (THF) yields a yellow suspension of 2. With ...

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