Synthesis of fluorinated analogs of geraniol

…, PL Wiggins, TL Plummer

Index: Poulter, C. Dale; Wiggins, Paul L.; Plummer, Thomas L. Journal of Organic Chemistry, 1981 , vol. 46, # 8 p. 1532 - 1538

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Citation Number: 56

Abstract

Results and Discussion 3-(Fluoromethyl) geraniol (4). A stereoselective synthesis of 3- (fluoromethy1) geraniol (4) is presented in Scheme I. The key reaction is the conjugate addition of the 4-methylpent-3-en-1-yl moiety (C6HI1) to acetylenic ester 1. This step establishes the correct stereochemistry

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ethyl (Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dienoate Structure

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3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

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(Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dien-1-yl acetate Structure

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ethyl (Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dienoate Structure

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N/A Structure

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acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

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ethyl (Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dienoate Structure

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acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

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(Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dien-1-yl acetate Structure

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2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

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acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

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ethyl (Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dienoate Structure

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