Cover Picture: Turning Spiroketals Inside Out: A Rearrangement Triggered by an Enol Ether Epoxidation (ChemistryOpen 5/2015)

ChemistryOpen

Chris Lorenc²  Dr. Josep Saurí¹  Arvin Moser⁵  Dr. Alexei V. Buevich¹  Dr. Antony J. Williams³  Dr. R. Thomas Williamson¹  Dr. Gary E. Martin⁴ 

[1] Process & Analytical Chemistry, NMR Structure Elucidation, Merck Research Laboratories, NJ, USA;Department of Chemistry, University of Connecticut, CT, USA;ORCID:orcid.org/0000-0002-2668-4821;ORCID:orcid.org/0000-0003-0750-3041;Advanced Chemistry Development, Inc., ON, Canada

关键词: cheminformatics;    computer-assisted structure elucidation;    NMR spectroscopy;    rearrangement;    spiro compounds;    spiroketals;   

DOI  :  10.1002/open.201500185

来源: Wiley

【 摘 要 】

Abstract

The cover picture compares the rearrangement of a small molecule to the process of turning a stuffed animal inside out. The recycled, inside-out stuffed animals are both artistic and philosophically provocative. They capture the essence of the rearrangement reaction because the compounds themselves turn inside out throughout the reaction, extending the diversity of products that can arise from simple starting materials. The epoxidation of some highly functionalized spiroketal compounds promoted rearrangements of their structures that turned them inside out. Some of the features of the products led the team to use X-ray crystallography and computer-assisted structure elucidation, computation, and a new version of the 1,1-ADEQUATE NMR experiment to determine their structures. More information can be found in the Communication by Mark W. Peczuh et al. (DOI: 10.1002/open.201500122).

【 授权许可】

Unknown   
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim