We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Dimerization Behavior of Substituted Bicyclo[3.1.0]hex-1-ene Derivatives.
- Authors
Zheng, Jun‐Cheng; Liu, Huaqing; Lee, Nam‐Kyu; Lee, Daesung
- Abstract
The different reaction profiles of lithium trimethylsilyldiazomethane with various 4-alkenyl ketones are described. It was found that the individual steps along the reaction pathway including a Brook rearrangement, elimination of lithium trimethylsilanolate to form alkylidene carbenes, and their addition to an alkene to form strained bicyclo[3.1.0]hex-1-ene derivatives were significantly affected by the substituents near or on the alkene moiety. Especially, the dimerization of bicyclo[3.1.0]hex-1-enes depends critically on the substituent pattern of the alkene, which controls the reaction to proceed in a concerted or a stepwise manner. On the basis of X-ray diffraction analysis, the dimers, which are of unprecedented structural complexity, were unambiguously elucidated.
- Subjects
DIMERIZATION; OLIGOMERIZATION; LITHIUM; ALKALI metals; DIAZOMETHANE
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 3, p506
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301575