Keywords
1
2-dihydro-3H-pyrrole-3-thiones
amino ynones
heterocyclization.
nucleophilic addition
secondary phosphine sulfides
Abstract
Unknown reactivity patterns of P=S and C=O bonds were observed when γ-amino α, β-ynones reacted with secondary phosphine sulfides affording, instead of the addition/ cyclization products, 1,2-dihydro-3H-pyrrole-3-thiones and the corresponding secondary phosphine oxides. The reaction mechanism involves the sulfur/oxygen exchange between the P=S and C=O functions. This is the first case of the successful competition between the P=S and P-H moieties as nucleophiles for electrophilic triple bond.
Funders
Ministry of Education and Science of the Russian Federation
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