| LDR | | 00000nam u2200205 4500 |
| 001 | | 000000432423 |
| 005 | | 20200224130001 |
| 008 | | 200131s2019 ||||||||||||||||| ||eng d |
| 020 | |
▼a 9781088366110 |
| 035 | |
▼a (MiAaPQ)AAI13900474 |
| 040 | |
▼a MiAaPQ
▼c MiAaPQ
▼d 247004 |
| 082 | 0 |
▼a 547 |
| 100 | 1 |
▼a Trongsiriwat, Nisalak. |
| 245 | 10 |
▼a Part I: The Study of 2-Aryl-1,3-Dithiane Derivatives As Pronucleophiles in Palladium-Catalyzed Allylic Alkylation and Propellylation Part II: Ligand-Free Palladium-Catalyzed Allylic Amintion of Hydrazone Derivatives Part III: Synthesis of Criegee Intermediate Precursors. |
| 260 | |
▼a [S.l.]:
▼b University of Pennsylvania.,
▼c 2019. |
| 260 | 1 |
▼a Ann Arbor:
▼b ProQuest Dissertations & Theses,
▼c 2019. |
| 300 | |
▼a 275 p. |
| 500 | |
▼a Source: Dissertations Abstracts International, Volume: 81-05, Section: B. |
| 500 | |
▼a Advisor: Walsh, Patrick J. |
| 502 | 1 |
▼a Thesis (Ph.D.)--University of Pennsylvania, 2019. |
| 506 | |
▼a This item must not be sold to any third party vendors. |
| 520 | |
▼a Chapter 1 and 2 detail studies of 2-aryl-1,3-dithianes as pronucleophiles in palladium-catalyzed allylic alkylation and propellylation to access skeletally diverse aryl alkyl ketone cores. Allylic carbonate and [1.1.1]propellane electrophiles successfully couple with in situ generated 2-sodio-1,3-dithiane nucleophiles to afford the corresponding products in good to excellent yields. Deprotection of these products leads to valuable aryl alkyl ketones. The palladium-catalyzed allylic alkylation of 2-aryl-1,3-dithianes is examined in chapter 1. A direct synthesis of ---棺,款-unsaturated ketones via a one-pot allylation-oxidation protocol is also presented. Additionally, the utility of this method is demonstrated through a sequential one-pot allylation-Heck cyclization to produce asterogynin derivatives which are important bioactive compounds in medicinal chemistry.Chapter 2 discloses a general method for the synthesis of bicyclo[1.1.1]pentane (BCP)-containing dithianes which, upon deprotection, provide access to BCP analogues of medicinally abundant diarylketones. Transformation of the dithiane part into a variety of functional groups such as BCP aryl difluoromethanes and BCP esteare demonstrated. A computational study indicates that the reaction of 2-aryl-1,3-dithianes and [1.1.1]propellane proceeds via a two-electron pathway.Chapter 3 focuses on a protocol for ligand-free palladium catalyzed allylic amination of in situ generated hydrazone nucleophiles at room temperature. This method is effective and applicable for a variety of hydrazones in excellent yields and also economical due to low palladium loading and ligand-free conditions. In addition, we demonstrated an example of tandem allylation-Fischer indole cyclization to afford the core structure of antifungal drug.In chapter 4, we introduce detailed on novel synthesis of (Z/E)-1,3-diiodobut-2-ene and (E)-1,3-diiodo-2-methylprop-1-ene which are considered as precursors of Criegee intermediates methyl vinyl ketone oxide (MVK-oxide) and methacrolein oxide (MARC-oxide) respectively. |
| 590 | |
▼a School code: 0175. |
| 650 | 4 |
▼a Inorganic chemistry. |
| 650 | 4 |
▼a Organic chemistry. |
| 690 | |
▼a 0488 |
| 690 | |
▼a 0490 |
| 710 | 20 |
▼a University of Pennsylvania.
▼b Chemistry. |
| 773 | 0 |
▼t Dissertations Abstracts International
▼g 81-05B. |
| 773 | |
▼t Dissertation Abstract International |
| 790 | |
▼a 0175 |
| 791 | |
▼a Ph.D. |
| 792 | |
▼a 2019 |
| 793 | |
▼a English |
| 856 | 40 |
▼u http://www.riss.kr/pdu/ddodLink.do?id=T15492194
▼n KERIS
▼z 이 자료의 원문은 한국교육학술정보원에서 제공합니다. |
| 980 | |
▼a 202002
▼f 2020 |
| 990 | |
▼a ***1008102 |
| 991 | |
▼a E-BOOK |