Solutions_Manual_for_Organic_Chemistry_6th_Ed 411

Solutions_Manual_for_Organic_Chemistry_6th_Ed 411 - eth...

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18-14 Trimethylphosphine has a-hydrogens that could be removed by butyllithium, generating undesired ylides. CH3 1+ BuLi CH3 1+ - CH3 1 + CH3-P-CH 2 R 1 CH -P-CHR + 3 1 CH -P-CH R 2 1 2 CH3 CH 3 desired ylide CH3 wrong ylide rotation .. + : h PPh3 \ \ \ I" H '" I I I H Me Me :O -- -! PPh) / H I I I I I I C _ C "" " H + Ph 3 PO .. .. . .. f- - " , 1.:1:1 . I I I Me "" "" - ' Me H ', r� / I H Me Me cis-2-butene The stereochemistry is inverted. The nucleophile triphenylphosphine must attack the epoxide in an
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