Preparation, Characterization and Reactivity of (3-Methylpentadienyl)iron(1+) Cations

Authors

Subhabrata Chaudhury, Marquette University
Shukun Li, Marquette University
Dennis W. Bennett, University of Wisconsin - MilwaukeeFollow
Tasneem Siddiquee, University of Wisconsin - MilwaukeeFollow
Daniel T. Haworth, Marquette UniversityFollow
William Donaldson, Marquette UniversityFollow

Document Type

Article

Language

eng

Publication Date

2007

Publisher

American Chemical Society

Source Publication

Organometallics

Source ISSN

0276-7333

Abstract

The title cations (9 and 12) were prepared by dehydration of (3-methyl-2,4-pentadien-1-ol)Fe(CO)₂L⁺ complexes. The structure of the (CO)₂PPh₃-ligated 12 was determined by single-crystal X-ray analysis. Reaction of carbon and heteroatom nucleophiles to (3-methylpentadienyl)Fe(CO)₃⁺ cations 9 and 12 proceeds either via attack at the dienyl terminus to give (3-methyl-1,3Z-diene)iron complexes or via attack at the internal carbon, followed by carbon monoxide insertion and reductive elimination to afford 3-methyl-4-substituted cyclohexenones. Cyclohexenone formation was found to be prevalent for addition of stabilized nucleophiles with strongly dissociated counterions to cation 9 (L = CO). Reaction of cation 9 with sodium bis[(−)-8-phenylmenthyl] malonate gave a single diastereomeric cyclohexenone.

Comments

Accepted version. Organometallics, Vol. 26. No. 22 (2007) pp 5295-5303. DOI. © 2007 American Chemical Society. Used with permission.

Recommended Citation

Chaudhury, Subhabrata; Li, Shukun; Bennett, Dennis W.; Siddiquee, Tasneem; Haworth, Daniel T.; and Donaldson, William, "Preparation, Characterization and Reactivity of (3-Methylpentadienyl)iron(1+) Cations" (2007). Chemistry Faculty Research and Publications. 50.
https://epublications.marquette.edu/chem_fac/50