Date of Award
2009
Document Type
Thesis
Publication Status
Version of Record
Submission Date
October 2026
Abstract
The conversion of alkynyl carbonyls to allenyl carbonyls via manganese mediated coordination followed by a base-catalyzed isomerization was carried out using a range of chiral and achiral amine bases. Chiral amidine and chiral DBU derivatives were synthesized to carry out the isomerization enantioselectively. We employed HPLC equipped with a chiral column to determine the enantiomeric excess. We also proved that the mechanism of that the manganese-coordinated alkyne/allene rearrangement reaction involved an intermediate cumenolate. It was also confirmed that amine base with pKa lower than that of DBU (pKa = 13.6) would not carry out the isomerization. Alkoxy base were also used in isomerization and the mechanism was also investigated.
Extent
xiii, 111 p. : ill. (some col.).
Recommended Citation
He, Chang., "Studies towards a catalytic asymmetric isomerization of manganese complexed alkynes to allenes using chiral bases" (2009). Electronic Theses and Dissertations 2000 - 2009. 1788.
https://digitalcommons.fau.edu/etd_general_5/1788
Identifier
FADT192983
Comments
by Chang He.|Thesis (M.S.)--Florida Atlantic University, 2009.|Includes bibliography.|Electronic reproduction. Boca Raton, Fla., 2009. Mode of access: World Wide Web.|by Chang He.