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Synthesis and reactions of some carbomethoxy-substituted cycloheptadiene-tricarbonyl iron complexes

Burello, Marco Paolo
http://rave.ohiolink.edu/etdc/view?acc_num=case1055529609

Abstract Details

1991, Doctor of Philosophy, Case Western Reserve University, Chemistry.
1-carbomethoxy(cyclohepta-1,3-diene)tricarbonyliron 1 and 2-carbomethoxy-(cyclohepta-1,3-diene)tricarbonyliron 2 were prepared in good yield from 2-carbomethoxy-cyclohept-1,3-diene by complexation with pentacarbonyliron or diiron nonacarbonyl. The corresponding dienyl salts 3 and 4 respectively were prepared by hydride abstaction with triphenylmethyl hexafluorophosphate. A range of nucleophiles including dimethyl malonate, nitrile, hydride and thiophenoxide were added to these dienyl salts and some interesting regiochemical results were observed. Addition of dimethyl malonate to both of the dienyl complexes gave a σ-π-allyl complex such as 5 as product. In all previous cases, addition of dimethyl malonate went at the terminus of the dienyl system to give a diene complex. In order to explain this unusual observation 13C NMR studies and extended Huckel calculations were done on some model dienyl complexes to determine charge densities and LUMO coefficients for the carbons of the dienyl system. Also, a classical resolution of the complexes was accomplished via the corresponding caboxylic acid-substituted complex.
Anthony Pearson (Advisor)
137 p.
Synthesis reactions carbomethoxy-substituted cycloheptadiene-tricarbonyl iron complexes

Recommended Citations

Citations

  • Burello, M. P. (1991). Synthesis and reactions of some carbomethoxy-substituted cycloheptadiene-tricarbonyl iron complexes [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1055529609

    APA Style (7th edition)

  • Burello, Marco. Synthesis and reactions of some carbomethoxy-substituted cycloheptadiene-tricarbonyl iron complexes. 1991. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1055529609.

    MLA Style (8th edition)

  • Burello, Marco. "Synthesis and reactions of some carbomethoxy-substituted cycloheptadiene-tricarbonyl iron complexes." Doctoral dissertation, Case Western Reserve University, 1991. http://rave.ohiolink.edu/etdc/view?acc_num=case1055529609

    Chicago Manual of Style (17th edition)

case1055529609
466
© 1991, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.