SYNTHESIS OF SOME NEW α,α-DIOXOKETENE-N,S- AND -N,N-ACETALS DERIVED FROM SECONDARY ALIPHATIC AMINES

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AL ADIWISH WEDAD M.; YAMIN B.M.; YAACOB W.A.

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ISSN: 2588-4824

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Journal: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS) Year:621 | Volume:10 | Issue:5 Page(s): 897-905

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Title

SYNTHESIS OF SOME NEW α,α-DIOXOKETENE-N,S- AND -N,N-ACETALS DERIVED FROM SECONDARY ALIPHATIC AMINES

Author(s)

AL ADIWISH WEDAD M. | YAMIN B.M. | YAACOB W.A. | Issue Writer Certificate

Keywords

α-DIOXOKETENE- N

S - AND α

α-DIOXOKETENE- N

N –ACETALS

SECONDARY ALIPHATIC AMINES

MONO- AND DOUBLE SUBSTITUTIONS

NUCLEOPHILIC ADDITION–ELIMINATION

Abstract

A total of 11 new a,a-dioxoketene- N,S -acetals (2a–2k) and two new a,a-dioxoketene- N,N -acetals (3j and 3k) have been synthesised by treating 3-[bis(methylthiol)methylene]pentane-2,4-dione (1) with increasing mole ratios of SECONDARY ALIPHATIC AMINES at room temperature, in either toluene or ethanol. Eight non-cyclic N -methylalkyl and N -ethylalkyl amines and the azacyclopentane of pyrrolidine yielded exclusively mono-substituted N,S -acetals (2a–2i), while the azacyclohexanes of piperidine and morpholine yielded the mono-substituted N,S -acetals 2j and 2k and the double-substituted N,N -acetals 3j and 3k. The conversion yields for the reactions in ethanol are considerably higher than those in toluene. Furthermore, the SECONDARY ALIPHATIC AMINES with an N -methylalkyl moiety, which have one primary a-carbon and less steric crowding around the nucleophilic nitrogen, appear to be more reactive towards 1 than those with the N -ethylalkyl group, which have two primary a-carbons; further, the latter amines are more reactive than the amines with secondary a-carbons.

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