22780-14-9

Upstream product

• 61136-72-9 3,3-Dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl trifluoromethane-sulfonate 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 61136-72-9 1-camphenyl triflate 
• 64-17-5 ethanol 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 140147-15-5 (1R)-3,3-dimethyl-2-methylenenorborn-1-yl triflate 
• 13487-72-4 (1R)-3,3-dimethyl-2-methyliden-1-norbornylamine 
• 7732-18-5 water 

Downstream Products

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 1925-51-5 (1R,4R)-1-hydroxymethyl-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one 
• 50-00-0 formaldehyd 

Relevant academic research and scientific papers

A new highly efficient synthetic route to enantiopure 10-bromocamphor

A new enantiospecific synthetic route to the interesting chiral synthetic intermediate 10-bromocamphor starting from readily available camphor is described. The procedure takes place straightforwardly in only three synthetic steps with high overall yield. Mechanistically, two interesting enantiospecific Wagner-Meerwein rearrangements involving 2-norbornyl carbocations take place during the process. Copyright (C) 2000 Elsevier Science Ltd.

A new straightforward preparation of enantiopure 10-hydroxycamphor

The enantiospecific preparation of the interesting chiral source 10-hydroxycamphor from commercially available camphor is described. The synthetic procedure takes place straightforwardly in only three synthetic steps with a high overall yield. The key step of the described route is based on the ability of a 2-methylenenorbornane intermediate to undergo an enantiospecific Wagner-Meerwein rearrangement under electrophilic treatment with m-CPBA.

UNUSUAL REACTIVITY OF NORBORNANE BRIDGEHEAD DERIVATIVES

The solvolysis of 2,2,3- and 2,3,3-trimethyl substituted 1-norbornyl triflates 1 and 6 in 60percent aqueous ethanol at 60 deg C proceeds via novel ?-bridged carbocations affording products mainly from hitherto unknown Wagner-Meerwein rearrangement and fragmentation reactions, respectively.

Synthesis of Bridgehead Derivatives; 1. Preparation of Substituted Bicycloheptan-1-ols and the Corresponding Trifluoromethanesulfonates

The reaction of substituted bicycloheptan-2-ones 1 with trifluoromethanesulfonic anhydride (Tf2O) yields bridgehead trifluoromethanesulfonates (triflates, 2).Both the reduction with lithium aluminum hydride and the alkaline hydrolysis of 2 affords the corresponding bridgehead alcohols 3 in good yields.