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Sigmatropic Rearrangements Accompanying the Addition of Dichlorocarbene to Norbornadiene
✍ Scribed by Charles W. Jefford; Gérald Bernardinelli; Jean-Claude Rossier; Jacques A. Zuber
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- German
- Weight
- 160 KB
- Volume
- 65
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
A new product arising from the reaction of dichlorocarbene with norbornadiene, 6__endo__‐(2,2‐dichlorovinyl)‐cis‐bicyclo[3.1.0]hex‐2‐ene, is described. It does not arise from the normal exo‐l,2‐adduct, but possibly originates by sigmatropic rearrangement of an initially formed zwitterionic intermediate.
📜 SIMILAR VOLUMES
## Abstract The title reactions have been investigated in a static system. The addition of acetylene to cyclopentadiene (CPD) results in formation of norbornadiene (BCH), cycloheptatriene (CHT), and toluene (T), while BCH decomposition produces CPD, C~2~H~2~, CHT, and T. Kinetic studies, comprising
The (Z)-(iodovinyl)oxetane 12 was prepared from d-glucose and the acyclic analog 18 was obtained from d-mannitol. Following the generation of their lithium derivatives by halogen-metal exchange, coupling to the enantiopure vinylsubstituted norbornanones 20, 23, and 29 proceeded exclusively via endo