Base-induced elimination reactions. VII. Hydroxide-promoted elimination reactions: alkyl halides as substrates

HCl and HBr were easily abstracted from secondary and tertiary alkyl halides by KOH in tetraglyme, but primary alkyl halides yielded approx. equal amts. of elimination and substitution products (alkenes and alcs. and/or ethers). However, the addn. of catalytic amts. of Me3N favored dehydrohalogenation via quaternary ammonium salt intermediates. [on SciFinder (R)]


Published in:
Helvetica Chimica Acta, 60, 8, 3060-8
Year:
1977
Keywords:
Note:
CAN 88:89011
23-3
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0018-019X
written in English.
75-50-3; 75-57-0; 506-59-2; 593-81-7; 5882-44-0; 15925-18-5; 16645-06-0 Role: CAT (Catalyst use), USES (Uses) (catalysts, for dehydrohalogenation of alkyl halides); 111-85-3; 628-61-5; 931-78-2 Role: RCT (Reactant), RACT (Reactant or reagent) (dehydrochlorination of, by potassium hydroxide and alkoxides); 111-83-1; 557-35-7 Role: RCT (Reactant), RACT (Reactant or reagent) (dehydrochlorination of, with potassium hydroxide and alkoxides); 2083-68-3P; 32359-06-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and decompn. of); 5706-90-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and stereoselective dehydrochlorination of); 5706-91-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 865-33-8; 865-47-4; 917-58-8; 1310-58-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with alkyl halides); 143-24-8 Role: RCT (Reactant), RACT (Reactant or reagent) (solvent, for dehydrohalogenation of alkyl halides by potassium hydroxide)
Laboratories:




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