1,2-elimination of alcohol from homoallyl ethers under the influence of mixed metal bases
1990
Abstract
Lithium diisopropylamide in the presence of catalytic amts. of potassium tert-butoxide smoothly converts homoallyl or homobenzyl type ethers to dienes or styrenes. g,d-Unsatd. acetals give 1,3-dienyl ethers and 4-alkylidenetetrahydropyrans or dihydropyrans produce a variety of dienols. If there is a choice, the new double bond is formed with high trans selectivity while the configuration of existing double bonds is retained. The elimination mode is syn-periplanar and concerted, though E1cb like. [on SciFinder (R)]
Details
Title
1,2-elimination of alcohol from homoallyl ethers under the influence of mixed metal bases
Author(s)
Margot, Christian ; Rizzolio, Michele ; Schlosser, Manfred
Published in
Tetrahedron
Volume
46
Issue
7
Pages
2411-2424
Date
1990
ISSN
0040-4020
Keywords
Note
CAN 113:96684
21-2
General Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
20262-14-0 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with dihydropyrancarboxaldehyde); 13417-49-7 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with methylethanide); 35192-73-5 (1-Nonen-4-ol) Role: RCT (Reactant), RACT (Reactant or reagent) (alkylation of); 3136-02-5 (2-Chlorotetrahydropyran) Role: RCT (Reactant), RACT (Reactant or reagent) (butenylation of); 763-32-6 (3-Methyl-3-buten-1-ol) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with acetaldehyde); 66-25-1 (Hexanal) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with butene); 106-98-9 (1-Butene); 624-64-6 (trans-2-Butene) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with hexanal); 75-07-0 (Acetaldehyde); 123-38-6 (Propanal); 590-86-3 Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with methylbutenol); 123-35-3 (Myrcene) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with paraformaldehyde); 3174-74-1; 4203-45-6 (2-Allyltetrahydropyran); 10066-31-6; 16302-35-5; 72184-93-1 (4,4-Diethoxy-3-methyl-1-butene) Role: RCT (Reactant), RACT (Reactant or reagent) (elimination reaction of); 111-66-0 (1-Octene) Role: RCT (Reactant), RACT (Reactant or reagent) (methoxymethylation of); 35836-73-8 Role: RCT (Reactant), RACT (Reactant or reagent) (methylation of); 29943-42-8 (4-Tetrahydropyranone) Role: RCT (Reactant), RACT (Reactant or reagent) (methylenation of); 1572-08-3P; 40930-20-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and butylation of); 36838-71-8P (4-Methylenetetrahydropyran); 55130-15-9P; 55873-95-5P; 59848-65-6P; 59848-66-7P; 59848-69-0P; 63500-68-5P; 63500-69-6P; 63500-70-9P (2-Ethyl-4-methylenetetrahydropyran); 71189-05-4P; 74481-27-9P; 90246-13-2P (4-Methoxy-1-nonene); 97847-43-3P; 97847-47-7P (2-Methyl-4-methylenetetrahydropyran); 97847-50-2P (cis-1-Methoxy-3-nonene); 128838-76-6P (3-Methoxymethyl-1-octene); 128838-78-8P; 128838-79-9P; 128838-83-5P (4-Ethoxy-1-nonene); 128838-84-6P; 128838-85-7P (4-Trimethylsilyloxy-1-nonene); 128838-86-8P (4-(Methoxymethoxy)-1-nonene); 128838-87-9P (4-Pivaloyloxy-1-nonene) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and elimination reaction of); 52922-22-2P; 52922-27-7P; 58558-46-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and methylation of); 300-57-2P (Allylbenzene); 766-90-5P; 873-66-5P; 3439-99-4P; 14314-21-7P; 15732-93-1P; 15732-94-2P; 30293-06-2P; 56700-77-7P; 59163-76-7P; 65442-32-2P; 71885-98-8P; 77192-27-9P; 87832-31-3P; 88888-64-6P; 93847-20-2P; 93884-50-5P; 97847-44-4P; 97847-45-5P; 97847-46-6P; 97847-48-8P; 97847-49-9P; 128838-73-3P; 128838-74-4P; 128838-75-5P; 128838-77-7P; 128838-80-2P; 128838-81-3P; 128838-82-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 590-18-1 (cis-2-Butene) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with hexanal or chlorotetrahydropyran); 865-47-4 (Potassium tert-butoxide) Role: RCT (Reactant), RACT (Reactant or reagent) (reagent from lithium diisopropylamide and, for elimination reactions of homoallyl ethers); 4111-54-0 (Lithium diisopropylamide); 38227-87-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reagent from potassium tert-butoxide and, for elimination reactions of homoallyl ethers)
21-2
General Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
20262-14-0 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with dihydropyrancarboxaldehyde); 13417-49-7 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with methylethanide); 35192-73-5 (1-Nonen-4-ol) Role: RCT (Reactant), RACT (Reactant or reagent) (alkylation of); 3136-02-5 (2-Chlorotetrahydropyran) Role: RCT (Reactant), RACT (Reactant or reagent) (butenylation of); 763-32-6 (3-Methyl-3-buten-1-ol) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with acetaldehyde); 66-25-1 (Hexanal) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with butene); 106-98-9 (1-Butene); 624-64-6 (trans-2-Butene) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with hexanal); 75-07-0 (Acetaldehyde); 123-38-6 (Propanal); 590-86-3 Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with methylbutenol); 123-35-3 (Myrcene) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with paraformaldehyde); 3174-74-1; 4203-45-6 (2-Allyltetrahydropyran); 10066-31-6; 16302-35-5; 72184-93-1 (4,4-Diethoxy-3-methyl-1-butene) Role: RCT (Reactant), RACT (Reactant or reagent) (elimination reaction of); 111-66-0 (1-Octene) Role: RCT (Reactant), RACT (Reactant or reagent) (methoxymethylation of); 35836-73-8 Role: RCT (Reactant), RACT (Reactant or reagent) (methylation of); 29943-42-8 (4-Tetrahydropyranone) Role: RCT (Reactant), RACT (Reactant or reagent) (methylenation of); 1572-08-3P; 40930-20-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and butylation of); 36838-71-8P (4-Methylenetetrahydropyran); 55130-15-9P; 55873-95-5P; 59848-65-6P; 59848-66-7P; 59848-69-0P; 63500-68-5P; 63500-69-6P; 63500-70-9P (2-Ethyl-4-methylenetetrahydropyran); 71189-05-4P; 74481-27-9P; 90246-13-2P (4-Methoxy-1-nonene); 97847-43-3P; 97847-47-7P (2-Methyl-4-methylenetetrahydropyran); 97847-50-2P (cis-1-Methoxy-3-nonene); 128838-76-6P (3-Methoxymethyl-1-octene); 128838-78-8P; 128838-79-9P; 128838-83-5P (4-Ethoxy-1-nonene); 128838-84-6P; 128838-85-7P (4-Trimethylsilyloxy-1-nonene); 128838-86-8P (4-(Methoxymethoxy)-1-nonene); 128838-87-9P (4-Pivaloyloxy-1-nonene) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and elimination reaction of); 52922-22-2P; 52922-27-7P; 58558-46-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and methylation of); 300-57-2P (Allylbenzene); 766-90-5P; 873-66-5P; 3439-99-4P; 14314-21-7P; 15732-93-1P; 15732-94-2P; 30293-06-2P; 56700-77-7P; 59163-76-7P; 65442-32-2P; 71885-98-8P; 77192-27-9P; 87832-31-3P; 88888-64-6P; 93847-20-2P; 93884-50-5P; 97847-44-4P; 97847-45-5P; 97847-46-6P; 97847-48-8P; 97847-49-9P; 128838-73-3P; 128838-74-4P; 128838-75-5P; 128838-77-7P; 128838-80-2P; 128838-81-3P; 128838-82-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 590-18-1 (cis-2-Butene) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with hexanal or chlorotetrahydropyran); 865-47-4 (Potassium tert-butoxide) Role: RCT (Reactant), RACT (Reactant or reagent) (reagent from lithium diisopropylamide and, for elimination reactions of homoallyl ethers); 4111-54-0 (Lithium diisopropylamide); 38227-87-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reagent from potassium tert-butoxide and, for elimination reactions of homoallyl ethers)
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LSCO
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Peer-reviewed publications
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Record creation date
2006-03-03