Generation and Trapping of Highly Strained Reactive Intermediate: Ethyl 1,2-Cyclohexadienecarboxylate

• Author / Creator

  Zhou, Sida

• Highly strained reactive intermediates can initiate chemical reactions and afford unique
  products. Cyclic allenes are important examples of such intermediates. Within the cyclic allene family, 1,2-cyclohexadiene was intensively studied over the years. In this dissertation, the investigation of developing practical methodology to generate and trap
  1-substituted-1,2-cyclohexadiene will be detailed.

  In Chapter 1, a brief history of strained reactive intermediates family is discussed, including benzynes and cycloalkynes, in addition to the development of 1,2-cyclohexadiene chemistry. The discovery of 1,2-cyclohexadiene, the study on its structure and properties and some known

  1-substituted cyclohexa-1,2-dienes will be discussed. A brief introduction of existing methods to generate and trap 1-subsituted cyclohexa-1,2-diene is described at the beginning of Chapter 2. Investigation of practical generation and trapping of ethyl 1,2-cyclohexadienecarboxylate, including systematic optimization of reaction conditions and exploration of the reaction scopes, is then discussed. The attempt to investigate the mechanism of newly discovered [2+2] cycloaddition between ethyl 1,2-cyclohexadienecarboxylate and alkynes will also be included.

• Subjects / Keywords

  • Cyclic allene
  • 1,2-cyclohexadiene

• Graduation date

  Fall 2015

• Type of Item

  Thesis

• Degree

  Master of Science

• DOI

  https://doi.org/10.7939/R3QR4P20N

• License

  This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.