Competing reaction pathways from α-halo-α-protioalkyl aryl sulfoxides initiated by organometallic reagents
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| Title: | Competing reaction pathways from α-halo-α-protioalkyl aryl sulfoxides initiated by organometallic reagents |
|---|---|
| Authors: | Blakemore, Paul R. paul.blakemore@science.oregonstate.edu, Burge, Matthew S.1, Sephton, Mark A.1 |
| Source: | Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Jun2007, Vol. 48 Issue 23, p3999-4002. 4p. |
| Subjects: | Solution (Chemistry), Aromatic amines, Alkylation, Chemical reactions |
| Abstract: | Abstract: The reactions of syn-1-haloethyl p-chlorophenyl sulfoxides (halogen=Cl, Br) with main-group organometallic reagents (n-BuMgCl, MeLi, n-BuLi, s-BuLi, and t-BuLi) in THF and PhMe solvents were examined. Product distributions were analyzed to determine the extent of competing sulfoxide ligand exchange, halogen–metal exchange, and deprotonation reaction pathways. A combination of t-BuLi in PhMe was optimal for initiation of sulfoxide ligand exchange from syn-1-chloroethyl p-chlorophenyl sulfoxide. [Copyright &y& Elsevier] |
| Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 25032703 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Competing reaction pathways from α-halo-α-protioalkyl aryl sulfoxides initiated by organometallic reagents – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Blakemore%2C+Paul+R%2E%22">Blakemore, Paul R.</searchLink><i> paul.blakemore@science.oregonstate.edu</i><br /><searchLink fieldCode="AR" term="%22Burge%2C+Matthew+S%2E%22">Burge, Matthew S.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Sephton%2C+Mark+A%2E%22">Sephton, Mark A.</searchLink><relatesTo>1</relatesTo> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Tetrahedron+Letters%3A+International+Organ+for+the+Rapid+Publication+of+Preliminary+Communications+in+Organic+Chemistry%22">Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry</searchLink>. Jun2007, Vol. 48 Issue 23, p3999-4002. 4p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Solution+%28Chemistry%29%22">Solution (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Aromatic+amines%22">Aromatic amines</searchLink><br /><searchLink fieldCode="DE" term="%22Alkylation%22">Alkylation</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reactions%22">Chemical reactions</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: Abstract: The reactions of syn-1-haloethyl p-chlorophenyl sulfoxides (halogen=Cl, Br) with main-group organometallic reagents (n-BuMgCl, MeLi, n-BuLi, s-BuLi, and t-BuLi) in THF and PhMe solvents were examined. Product distributions were analyzed to determine the extent of competing sulfoxide ligand exchange, halogen–metal exchange, and deprotonation reaction pathways. A combination of t-BuLi in PhMe was optimal for initiation of sulfoxide ligand exchange from syn-1-chloroethyl p-chlorophenyl sulfoxide. [Copyright &y& Elsevier] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1016/j.tetlet.2007.04.031 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 4 StartPage: 3999 Subjects: – SubjectFull: Solution (Chemistry) Type: general – SubjectFull: Aromatic amines Type: general – SubjectFull: Alkylation Type: general – SubjectFull: Chemical reactions Type: general Titles: – TitleFull: Competing reaction pathways from α-halo-α-protioalkyl aryl sulfoxides initiated by organometallic reagents Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Blakemore, Paul R. – PersonEntity: Name: NameFull: Burge, Matthew S. – PersonEntity: Name: NameFull: Sephton, Mark A. IsPartOfRelationships: – BibEntity: Dates: – D: 04 M: 06 Text: Jun2007 Type: published Y: 2007 Identifiers: – Type: issn-print Value: 00404039 Numbering: – Type: volume Value: 48 – Type: issue Value: 23 Titles: – TitleFull: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry Type: main |
| ResultId | 1 |
