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Enyne Metathesis–Oxidation Sequence for the Synthesis of 2‐Phosphono Pyrroles: Proof of the “Yne‐then‐Ene” Pathway
Author(s) -
Dieltiens Nicolai,
Moonen Kristof,
Stevens Christian V.
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600789
Subject(s) - enyne metathesis , ene reaction , metathesis , sequence (biology) , salt metathesis reaction , chemistry , stereochemistry , organic chemistry , biochemistry , polymerization , polymer
A new tandem reaction sequence has been developed for the synthesis of 2‐phosphono pyrroles. The sequence consists of ring‐closing enyne metathesis of a substituted aminophosphonate, containing a terminal alkyne and an internal alkene, in combination with in situ oxidation of the produced 3‐pyrrolines using tetrachloroquinone. By analyzing the formation of the end and certain byproducts, taking into account the difference in reactivity of different substrates and carefully studying spectroscopic data, it was found that the reaction proceeds by means of the “yne‐then‐ene” pathway. During the initiation phase, a new ruthenium carbene is formed which continues the propagation cycle.