Comments on the ring-opening polymerization of morpholine-2,5-dione derivatives by various metal catalysts and characterization of the products formed in the reactions involving R2SnX2, where X = OPri and NMe2 and R = Bun, Ph and p-Me 2NC6H4

M. H. Chisholm, J. Galucci, C. Krempner, C. Wiggenhorn

Research output: Contribution to journalReview article

19 Scopus citations

Abstract

(3S,6S)-3-Isopropyl-6-methyl-morpholine-2,5-dione (1), and (3S,6S)-3,6-dimethyl-morpholine-2,5-dione (2), do not enter into ring-opening polymerization reactions with metal catalyst precursors commonly employed for lactides, and with Sn(ii) octanoate, only low molecular weight oligomers are obtained. Reactions with R2SnX2 compounds, where R = Ph, Bun and p-Me2NC6H4 and X = OPr i or NMe2, reveal that ring-opening of the morpholine-2,5-diones does occur, but that polymerization is terminated by the formation of kinetically-inert products such as (Ph2Sn[μ, η3-OCH(Me)CONCH(Pri)COOPri])2 (3), and ([Bun)2Sn[μ,η3-OCH(Me)CONCH(Me) CONMe2])2 (4), with elimination of HX. Ph 3SnOPri is seen to react reversibly with morpholine-2,5-diones in toluene-d8 by 1H NMR spectroscopy while (Bun)3SnNMe2 reacts by ring opening to give (Bun)3SnOCH(Me)C(O)NHCHMeC(O)NMe2. The new organotin compounds have been characterized by 1H, 13C(1H) and 118Sn NMR spectroscopy and compounds 1, 2, 3 and 4 by single crystal X-ray crystallography.

Original languageEnglish
Pages (from-to)846-851
Number of pages6
JournalDalton Transactions
Issue number6
DOIs
StatePublished - 2006

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