ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
2,5-Bis(piperidinomethyl)pyrrole and (2,5-Pyrrolediyldimethylene)bis(triphenylphosphonium iodide): Synthesis and Reactions Leading to [2.2](2,5)Pyrrolophanes and 2,5-Bisvinylsubstituted PyrrolesMannich reaction of pyrrole results in the formation of 2,5-bis(piperidinomethyl)pyrrole (1a) which, after quaternization and treatment with cyanide, yields the stereoisomeric [2.2](2,5)pyrrolophanes 3a - c and 2,5-bis(cyanomethyl)pyrrole (1c). (2,5-Pyrrolediyldimethylene)bis(triphenylphosphonium iodide) (5a) and (2-pyrrolylmethyl)triphenylphosphonium iodide (8c) are obtained from the methiodides of 1a and 2-(dimethylaminomethyl)pyrrole (8a), respectively. They undergo Wittig reaction with aldehydes, but predominantly from substitution products if nucleophiles are present.
Notes:
Mannich-Reaktion an Pyrrol führt zu 2,5-Bis(piperidinomethyl)pyrrol (1a), das nach Quartärisierung und Umsetzung mit Cyanid neben 2,5-Bis(cyanmethyl)pyrrol (1c) die stereoisomeren [2.2](2,5)Pyrrolophane 3a - c liefert. Aus den Methiodiden von 1a und 2-(Dimethylaminomethyl)pyrrol (8a) werden (2,5-Pyrroldiyldimethylen)bis(triphenylphosphoniumiodid) (5a) sowie (2-Pyrrolylmethyl)triphenylphosphoniumiodid (8c) erhalten, die mit Aldehyden Wittig-Reaktionen eingehen, mit gleichzeitig vorhandenen Nucleophilen jedoch unter Substitution reagieren.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198519850916
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