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TRANSITION METAL CATALYZED REARRANGEMENT OF DIMETHYL VINYLCYCLOBUTENE DICARBOXYLATES DERIVATIVES TO DIMETHYL CYCLOHEXADIENE DICARBOXYLATES AND PHTHALATES

Lovchik, Martin Alan
http://rave.ohiolink.edu/etdc/view?acc_num=ucin1000127850

Abstract Details

2001, MS, University of Cincinnati, Arts and Sciences : Chemistry.
Vinylcyclobutene derivatives rearrange in the presence of transition metals to form cyclohexadienes and phthalates. Previous work in our group showed that this rearrangement could be performed with Ni(l), Ti(lll), Fe(ll), and Sm(ll). For this thesis, a large variety of metals was studied for these rearrangements. In addition, these methods were applied to various derivatives of vinylcyclobutene. It was found that Pd(ll) would promote the rearrangement to yield phthalates, in the same manner as Ti(lll) and Sm(ll). In addition, a new type of rearrangement was found. Methyl dereivatives of vinylcyclobutene, bearing a methyl substituent on the vinyl group, rearranged to form cyclopentadienes. X-Ray crystallography was used to prove the structure of the dimethyl derivative of vinylcyclobutene. The structures of the other synthesized compounds were confirmed by various spectroscopic analyses.
Allan Pinhas (Advisor)
VINYLCYCLOBUTENE; METAL PROMOTED REARRANGEMENT; Z+Z PHOTO-ADDITION; DECHLORINATION; ACTIVATED ZINC

Recommended Citations

Citations

  • Lovchik, M. A. (2001). TRANSITION METAL CATALYZED REARRANGEMENT OF DIMETHYL VINYLCYCLOBUTENE DICARBOXYLATES DERIVATIVES TO DIMETHYL CYCLOHEXADIENE DICARBOXYLATES AND PHTHALATES [Master's thesis, University of Cincinnati]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1000127850

    APA Style (7th edition)

  • Lovchik, Martin. TRANSITION METAL CATALYZED REARRANGEMENT OF DIMETHYL VINYLCYCLOBUTENE DICARBOXYLATES DERIVATIVES TO DIMETHYL CYCLOHEXADIENE DICARBOXYLATES AND PHTHALATES. 2001. University of Cincinnati, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ucin1000127850.

    MLA Style (8th edition)

  • Lovchik, Martin. "TRANSITION METAL CATALYZED REARRANGEMENT OF DIMETHYL VINYLCYCLOBUTENE DICARBOXYLATES DERIVATIVES TO DIMETHYL CYCLOHEXADIENE DICARBOXYLATES AND PHTHALATES." Master's thesis, University of Cincinnati, 2001. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1000127850

    Chicago Manual of Style (17th edition)

ucin1000127850
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© 2001, all rights reserved.
This open access ETD is published by University of Cincinnati and OhioLINK.