Bibliographic Citation
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Title | Some mercuration reactions of substituted pyrroles |
Creator/Author | Ganske, J.A. ; Pandey, R.K. ; Postich, M.J. ; Snow, K.M. ; Smith, K.M. (Univ. of California, Davis (USA)) |
Publication Date | 1989 Sep 29 |
OSTI Identifier | OSTI ID: 7071525 |
Other Number(s) | ISSN0022-3263; CODEN: JOCEA |
Resource Type | Journal Article |
Resource Relation | Journal of Organic Chemistry ; Vol/Issue: 54:20 |
Subject | 400201 -- Chemical & Physicochemical Properties; PYRROLES-- MERCURY ADDITIONS; DATA ANALYSIS;EXPERIMENTAL DATA;MEASURING INSTRUMENTS;MEASURING METHODS;PALLADIUM;SOLVENTS |
Related Subject | ALLOYS;AZOLES;DATA;ELEMENTS;HETEROCYCLIC COMPOUNDS;INFORMATION;MERCURY ALLOYS;METALS;NUMERICAL DATA;ORGANIC COMPOUNDS;ORGANIC NITROGEN COMPOUNDS;PLATINUM METALS;TRANSITION ELEMENTS |
Description/Abstract | Mercuration of N-unsubstituted pyrroles with mercury(II) acetate results in immediate precipitation of the N-mercurated derivative, which is insoluble in virtually all organic solvents.^If the pyrrole N atom is protected (e.g., with Me, CH{sub 2}OCH{sub 2}Ph, or CO{sub 2}t-Bu) then mercuration takes place efficiently at unsubstituted pyrrole carbons.^Subsequent palladium/olefin (Heck-type) reactions afford the corresponding pyrrole acrylate when, for example, the olefin is methyl acrylate, deprotection (when the N-substituent is CH{sub 2}OCH{sub 2}Ph or CO{sub 2}t-Bu) then affords the required carbon-substituted pyrrole.^Attempts to deprotect the N-methylpyrroles were unsuccessful. |
Country of Publication | United States |
Language | English |
Format | Pages: 4801-4807 |
System Entry Date | 2001 May 13 |
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