Synthesis

TBAF-Promoted Elimination of Vicinal Dibromides Having an Adjacent O-Functional Group: Syntheses of 2-Bromoalk-1-enes and Alkynes

N Kutsumura, K Kubokawa, T Saito

Index: Kutsumura, Noriki; Kubokawa, Keisuke; Saito, Takao Synthesis, 2011 , # 15 p. 2377 - 2382

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Citation Number: 3

Abstract

Reaction of dibromide 1a with 5.0 equivalents of base in N,N-dimethylformamide at 80 ˚C yielded some combination of 2-bromoalk-1-ene 2a and alkyne 3a. Most of the bases gave 2a in low to high yield and no 3a (Table [¹] , entries 3-8). The base cesium fluoride, which is moderately basic and whose fluoride exhibits low nucleophilicity, gave 2a in 79% yield together with 3a in 14% yield (Table [¹] , entry 9). Significantly, a solution of 1 M tetrabutylammonium fluoride ...