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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 Date1989 Sep 29
OSTI IdentifierOSTI ID: 7071525
Other Number(s)ISSN0022-3263; CODEN: JOCEA
Resource TypeJournal Article
Resource RelationJournal of Organic Chemistry ; Vol/Issue: 54:20
Subject400201 -- Chemical & Physicochemical Properties; PYRROLES-- MERCURY ADDITIONS; DATA ANALYSIS;EXPERIMENTAL DATA;MEASURING INSTRUMENTS;MEASURING METHODS;PALLADIUM;SOLVENTS
Related SubjectALLOYS;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 PublicationUnited States
LanguageEnglish
FormatPages: 4801-4807
System Entry Date2001 May 13

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