The Influence of the Substrate Structure in the Tellurocyclofunctionalization Reaction of g,d-Unsaturated Carboxylic Acids and their Corresponding Benzyl Esters
<FONT FACE=Symbol>g,d</FONT>-Unsaturated carboxylic acids containing monosubstituted double bonds react with aryltellurium trichlorides to give the expected tellurolactone. Reaction of the corresponding benzyl esters gives the addition product of the aryltellurium trichlorides to the double bond. <FONT FACE=Symbol>g,d</FONT>-Unsaturated carboxylic acids containing 1,1-disubstituted double bonds lead to a mixture of the expected tellurolactone and the product of hydrochloric acid addition to the double bond; the corresponding benzyl ester gives the tellurolactone as the only product. The stereoselectivity of the reaction is low; mixtures of the two possible diastereomeric lactones are formed in approximately 1:1 ratios.
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Sociedade Brasileira de Química
1998
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oai:scielo:S0103-505319980004000132002-10-30The Influence of the Substrate Structure in the Tellurocyclofunctionalization Reaction of g,d-Unsaturated Carboxylic Acids and their Corresponding Benzyl EstersMoraes,Denilson N.Santos,Rute A.Comasseto,João V. tellurocyclofunctionalization tellurolactones <FONT FACE=Symbol>g,d</FONT>-Unsaturated carboxylic acids containing monosubstituted double bonds react with aryltellurium trichlorides to give the expected tellurolactone. Reaction of the corresponding benzyl esters gives the addition product of the aryltellurium trichlorides to the double bond. <FONT FACE=Symbol>g,d</FONT>-Unsaturated carboxylic acids containing 1,1-disubstituted double bonds lead to a mixture of the expected tellurolactone and the product of hydrochloric acid addition to the double bond; the corresponding benzyl ester gives the tellurolactone as the only product. The stereoselectivity of the reaction is low; mixtures of the two possible diastereomeric lactones are formed in approximately 1:1 ratios.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.9 n.4 19981998-08-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531998000400013en10.1590/S0103-50531998000400013 |
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| author |
Moraes,Denilson N. Santos,Rute A. Comasseto,João V. |
| spellingShingle |
Moraes,Denilson N. Santos,Rute A. Comasseto,João V. The Influence of the Substrate Structure in the Tellurocyclofunctionalization Reaction of g,d-Unsaturated Carboxylic Acids and their Corresponding Benzyl Esters |
| author_facet |
Moraes,Denilson N. Santos,Rute A. Comasseto,João V. |
| author_sort |
Moraes,Denilson N. |
| title |
The Influence of the Substrate Structure in the Tellurocyclofunctionalization Reaction of g,d-Unsaturated Carboxylic Acids and their Corresponding Benzyl Esters |
| title_short |
The Influence of the Substrate Structure in the Tellurocyclofunctionalization Reaction of g,d-Unsaturated Carboxylic Acids and their Corresponding Benzyl Esters |
| title_full |
The Influence of the Substrate Structure in the Tellurocyclofunctionalization Reaction of g,d-Unsaturated Carboxylic Acids and their Corresponding Benzyl Esters |
| title_fullStr |
The Influence of the Substrate Structure in the Tellurocyclofunctionalization Reaction of g,d-Unsaturated Carboxylic Acids and their Corresponding Benzyl Esters |
| title_full_unstemmed |
The Influence of the Substrate Structure in the Tellurocyclofunctionalization Reaction of g,d-Unsaturated Carboxylic Acids and their Corresponding Benzyl Esters |
| title_sort |
influence of the substrate structure in the tellurocyclofunctionalization reaction of g,d-unsaturated carboxylic acids and their corresponding benzyl esters |
| description |
<FONT FACE=Symbol>g,d</FONT>-Unsaturated carboxylic acids containing monosubstituted double bonds react with aryltellurium trichlorides to give the expected tellurolactone. Reaction of the corresponding benzyl esters gives the addition product of the aryltellurium trichlorides to the double bond. <FONT FACE=Symbol>g,d</FONT>-Unsaturated carboxylic acids containing 1,1-disubstituted double bonds lead to a mixture of the expected tellurolactone and the product of hydrochloric acid addition to the double bond; the corresponding benzyl ester gives the tellurolactone as the only product. The stereoselectivity of the reaction is low; mixtures of the two possible diastereomeric lactones are formed in approximately 1:1 ratios. |
| publisher |
Sociedade Brasileira de Química |
| publishDate |
1998 |
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http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531998000400013 |
| work_keys_str_mv |
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1756403108801413120 |