Advanced precursors to novel ferrocene-based ligands Cp2FeC(O)CH(R)C(O)CH3 (R = benzyl, allyl) were synthesized from 1-ferrocenylbutane-1,3-dione via active methylene chemistry. Crystal structures were obtained and computational studies carried out to explore the structural features of these new compounds. Addition of carbonyl electrophiles resulted in the formation of unexpected products, which were identified and mechanisms for their formation proposed. (C) 2020 Elsevier Ltd. All rights reserved.

Issues of energy and sustainability are having a direct impact on the public and are capturing the interests of many. As result, it is no surprise that science, including the field of chemistry, will become more connected with society in the future. To address this connection, we are in the process of integrating important elements of renewable energy and sustainable chemistry across the undergraduate chemistry curriculum at the University of Minnesota, Morris. This project strives to create a curriculum which is more interdisciplinary with respect to both teaching and research and which introduces topics that are timely, yet essential in preparing undergraduate students. Our initial efforts are focused on three key areas: (i) developing new courses in renewable energy and sustainability; (ii) integrating photovoltaics across the undergraduate curriculum; and (iii) illustrating the role of biochemistry in renewable energy and sustainability. Our goal is to develop a far-reaching energy and sustainable chemistry curriculum that complements the traditional curriculum and better prepares our future graduates for success in addressing global problems. Overview of Project Renewable Energy Across the Curriculum • Add solar energy (PV) to existing courses • Develop 3000 level course on sustainable energy • Teach students the role of biochemistry in this area Sustainable Chemistry • Develop new course: Polymer Chem. and the Envt. • Add sustainable chemistry to existing courses • Teach students the role of biochemistry in this area Chem 3301: The Chemistry of Sustainable Energy Objectives • To demonstrate key role of chemistry in sustainable energy • To introduce and reinforce important chemistry concepts in the context of energy • Use the primary literature as a principal teaching instrument General Course Content • Background: Energy & fossil fuels • Polymer chemistry Composites (turbine blade materials) Solid electrolytes (fuel cells) • Fuel Cells Hydrogen generation Types of fuel cells • Biomass Types of biomass/types of biofuels Processes (gasification, digestion, pyrolysis, fermentation) • Photovoltaics Existing and future technologies Biochemistry Component Incorporating cellulosic ethanol into the undergraduate curriculum • Introductory organic lab: saccharification, fermentation of biomass to ethanol, use commercial cellulase enzymes, variety of feedstocks/pretreatment methods (Intro to Research students develop lab experiment) • Cellulosic ethanol unit added to Bioorganic Chemistry course (Advanced students – organic, biochemistry prerequisite) No textbook – focus on primary literature • Independent research: Goal: clone, express and characterize novel cellulases from uncultured microorganisms Overview and Activities Current and Future Activities

A series of experiments for undergraduate laboratory courses (e.g., organic, polymer, inorganic) have been developed. These experiments focus on understanding the regiochemistry of the conducting polymer poly(3-hexylthiophene) (P3HT). The substitution patterns in P3HTs control their conformational features, which, in turn, dictates the π conjugation and subsequent electronic properties of the materials. The regiochemistry in P3HTs can be controlled synthetically, and this experiment includes the synthesis of regioregular P3HT via Grignard metathesis chemistry. The regiochemistry is established unambiguously using techniques such as 1H NMR and UV−vis spectroscopy; comparisons to the regiorandom isomer are then made. Density functional theory calculations are also used to shed light on the electronic and conformational features of the polymers by analyzing suitable oligomers. These experiments illustrate the importance of regiochemistry in organic materials and expose students to a number of important chemical concepts as well as useful physical and theoretical methods.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTeaching Research: A Curriculum Model That WorksNancy E. Carpenter and Ted M. Pappenfus View Author Information Division of Science and Mathematics, University of Minnesota, Morris, Morris, MN 56267Cite this: J. Chem. Educ. 2009, 86, 8, 940Publication Date (Web):August 1, 2009Publication History Received3 August 2009Published online1 August 2009Published inissue 1 August 2009https://pubs.acs.org/doi/10.1021/ed086p940https://doi.org/10.1021/ed086p940research-articleACS PublicationsRequest reuse permissionsArticle Views867Altmetric-Citations21LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Biochemistry,Curriculum,Students,Teaching and learning methods,Undergraduates Get e-Alerts

AbstractSigmatropic rearrangements of allylic systems have found wide application in organic synthesis, with carbon‐carbon bond forming rearrangements such as the Cope and Claisen rearrangements being particularly well known. The sigmatropic rearrangement of allylic imidates offers a valuable entry into the preparation of protected allylic amines. Conversion of an imidate to the amide is essentially irreversible, with the transformation of the imidate to the amide being exothermic by about 15 kcal/mol. Since the discovery of the thermal allylic imidate rearrangement in 1937, a number of systems have been investigated for the practical preparation of allylic amines by this route. However, it was the discovery and development of the rearrangement of allylic trichloroacetamidates that demonstrated the utility of this synthetic method.This chapter is limited to the discussion of allylic trichloro‐ and trifluoracetamidate rearrangements. The [3,3]‐sigmatropic rearrangement of trichloracetamidates (now called the Overman rearrangement) or trifluoroacetimidates can be carried out either thermally or with Hg(II) or Pd(II) catalysis, The scope of this rearrangement is such that primary, secondary, and tertiary allylic amides are readily accessible, thus providing a wide entry into nitrogen‐containing products such as amino sugars, nucleotides, peptides, etc. The Overman rearrangement has found extensive application in the total synthesis of natural products. The recent development of the use of chiral Pd(II) catalysts bodes well for amine synthesis.

UV-vis irradiation of CpFe(CO)(2)[CHPh(OSiMe3)] (1b) in the presence of PPh3 produces eta(4)-{exo-C5H5[CHPh(OSiMe3)]}Fe(CO)(2)PPh3 (3b), the product of alkyl migration from iron to the Cp ring, in good yield.

AbstractThe enol triflates (I) undergo cyclization in the presence of palladium(II) acetate, forming the bicyclic dienones (II).