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SCOOPY and oxirane reactions: a-lithio-ylides vs. conventional ylides

Ph3P:CH2 reacted with epoxides I (R = H, Me, vinyl; R1 = H, Me) or cyclohexene oxide in the presence of 1.2 equiv LiX (X = Br, iodo, BPh4) to give Ph3P+CH2CH2CRR1OH X- or 83% trans-II. Similarly, Ph3P:CH, I (R = R1 = H) and LiBr gave 68% Ph3P+CHMeCH2CH2OHBr-. Thus it is unnecessary to use a-lithio-ylides. [on SciFinder (R)]

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