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26.7 Terpenes: The Isoprene Rule

26.7 Terpenes: The Isoprene Rule

www.columbia.edu

After CC Bond Formation... + OPP OPP The carbocation can lose a proton to give a double bond. –H + After CC Bond Formation... OPP This compound is called geranyl pyrophosphate. It can undergo hydrolysis of its pyrophosphate to give geraniol (rose oil). After CC Bond Formation... OPP OH Geraniol H 2 O.

  Bond, Formation, C bond formation

Professor J. Stephen Clark

Professor J. Stephen Clark

www.chem.gla.ac.uk

CC bond formation using enols, enolates, enamines R1 R2 O P2S5 R1 R2 S R SH R1 S R2 thioketones thiols thioethers OH O R H2N O NH2 H2N NH NH2 NH2 O R O O R1 R2 NH2 NH R O O R1 OR2 carboxylic acids amides amidines urea guanidine β-diketones β-keto esters. 13 General Strategies for Heterocycle Synthesis

  Bond, Formation, C bond formation

C-C BOND FORMATION 72 - Vanderbilt University

C-C BOND FORMATION 72 - Vanderbilt University

www.vanderbilt.edu

C-C BOND FORMATION 73 typical conditions: strong hindered (non-nucleophilic) base such as LDA R2NH pKa= ~30 N Li Ester Enolates- Esters are …

  University, Bond, Vanderbilt, Formation, Vanderbilt university, C c bond formation 72, C bond formation

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