22482-71-9

Usage

Type of compound

Bicyclic ketone

Derived from

Norcarane (a bicyclic hydrocarbon with a unique spirocyclic structure)

Primary use

Intermediate in the synthesis of various organic compounds

Potential applications

Medicinal chemistry and as a building block in the synthesis of novel pharmaceuticals

Unique structure

Spirocyclic structure

Reactivity

Valuable tool in organic synthesis and chemical research

Upstream product

• 279-19-6 nortricyclane 
• 75-36-5 acetyl chloride 
• 20647-99-8 1-(1-hydroxyethyl)tricyclo<2.2.1.0^2,6>heptane 
• 16219-75-3 2-ethylidenenorbornene 

Downstream Products

• 4696-13-3 1-Phenyl-1-<1-nortricyclyl>-aethylen 

Relevant academic research and scientific papers

34. Norbornanes Part 20 Inductivity and Bridging in 2-Norbornyl Cations

The solvolysis rates and products of several 1-substituted 2-exo- and 2-endo-norbornyl p-toluenesulfonates 7 and 8, respectively, have been determined.Hydrolyses of these epimeric tosylates yielded rearranged products in varying amounts, except when the substituent was COOCH3 or CN.The logarithms of the rate constants (log k) for the endo-series 8 correlated linearly with the corresponding inductive constants ?q1 with a reaction constant ρ1 of -1.24.On the other hand, log k values for the exo-series 7 appear to fit two regression lines,the first line (ρ1 = -1.90) defined by the tosylates that ionize, with rearrangement, to the tertiary cations 11, the second (ρ1 = -1.86) by the tosylates 7(R = H, COOCH3, and CN) that ionize to an asymetrically bridged secondary cation 19.These results confirm the unique participation of C(6) with a ρ1 of -2.00 in the ionization of 2-exo-norbornyl tosylate.