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Tandem Insertion/Rearrangements by Insertion of Rhodium Carbenes Into Sulfur Bonds and Metal-Catalyzed Insertion Into α-Diazocarbonyl Compounds.
Tandem Insertion/Rearrangements by Insertion of Rhodium Carbenes Into Sulfur Bonds and Metal-Catalyzed Insertion Into α-Diazocarbonyl Compounds.
- 자료유형
- 학위논문
- Control Number
- 0017162164
- International Standard Book Number
- 9798383598214
- Dewey Decimal Classification Number
- 547
- Main Entry-Personal Name
- Combs, Jason R.
- Publication, Distribution, etc. (Imprint
- [S.l.] : University of California, Irvine., 2024
- Publication, Distribution, etc. (Imprint
- Ann Arbor : ProQuest Dissertations & Theses, 2024
- Physical Description
- 381 p.
- General Note
- Source: Dissertations Abstracts International, Volume: 86-02, Section: B.
- General Note
- Advisor: Van Vranken, David L.
- Dissertation Note
- Thesis (Ph.D.)--University of California, Irvine, 2024.
- Summary, Etc.
- 요약This dissertation will focus on four main areas: The first aspect to be discussed will be reaction of allyl 2-diazo-2-phenylacetates with trimethylsilyl thioethers in the presence of rhodium(II) catalysts. These conditions generate α-allyl-α-thio silyl esters which undergo a spontaneous Ireland-Claisen rearrangement. Competing side-reactions, substrate scope and application will be explored.The second aspect to be discussed will be metal-catalyzed halogen insertion into α-diazocarbonyl compounds. Attempts to optimize the reaction and efforts to obtain asymmetric induction will be explored.The third aspect to be discussed will be rhodium(II)-catalyzed carbene transfer from trimethylsilyldiazomethane to arylmethyl thioethers, generating sulfonium ylides that undergo [2,3]-sigmatropic rearrangement, punching quaternary centers into aromatic rings. Substrate scope and competing side-reactions will be discussed.The final aspect to be discussed will be rhodium(II)-catalyzed carbene transfer from trimethylsilyldiazomethane to allylic thioesters, generating S-acyl allylsulfonium ylides that undergo [2,3]-sigmatropic rearrangement. This is the first report of an S-acyl Doyle-Kirmse reaction.
- Subject Added Entry-Topical Term
- Organic chemistry.
- Subject Added Entry-Topical Term
- Chemistry.
- Subject Added Entry-Topical Term
- Analytical chemistry.
- Index Term-Uncontrolled
- Diazocarbonyl compounds
- Index Term-Uncontrolled
- Arylmethyl thioether
- Index Term-Uncontrolled
- Rhodium carbenes
- Index Term-Uncontrolled
- Ireland-Claisen rearrangement
- Added Entry-Corporate Name
- University of California, Irvine Chemistry
- Host Item Entry
- Dissertations Abstracts International. 86-02B.
- Electronic Location and Access
- 로그인을 한후 보실 수 있는 자료입니다.
- Control Number
- joongbu:656144
