First example of the synthesis of N-vinylpyrrole from methoxy- allene and methoxyethyl isothio- cyanate: unprecedented elimination of methanol from a β-substituted methyl ethyl ether

Author: Nedolya N.   Tarasova O.   Albanov A.   Klyba L.   Trofimov B.  

Publisher: Springer Publishing Company

ISSN: 0009-3122

Source: Chemistry of Heterocyclic Compounds, Vol.46, Iss.1, 2010-05, pp. : 61-65

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Abstract

Using as example 3-methoxy-1-(2-methoxyethyl)-2-methylsulfanylpyrrole, obtained in one preparative stage from α-lithiated methoxyallene and 2-methoxyethyl isothiocyanate, a facile cleavage of a C–O bond in the N-(2-methoxyethyl) substituent by the t-BuOK–DMSO system has been discovered, opening access to a new class of N-vinylpyrroles (through β-elimination of methanol).

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