55373-77-8

Upstream product

• 497-38-1 Norbornan-2-on 
• 75-20-7 calcium carbide 
• 497-38-1 2-norbornanone 
• 1066-26-8 sodium acetylide 

Downstream Products

• 99075-36-2 (+/-)-carbamic acid-(2-ethynyl-[2endo]norbornyl ester) 
• 5019-82-9 bicyclo[3.2.1]octan-2-one 
• 14252-05-2 bicyclo[3.2.1]octan-3-one 
• 125011-13-4 (1R,4S)-2-Ethynyl-bicyclo[2.2.1]hept-2-ene 
• 125011-11-2 (1R,4S)-2-Ethynyl-2-phenoxy-bicyclo[2.2.1]heptane 
• 125011-12-3 (1R,4S)-2-Ethynyl-2-p-tolyloxy-bicyclo[2.2.1]heptane 
• 130907-53-8 (+/-)-carbonic acid-(2-ethynyl-[2endo]norbornyl ester)-phenyl ester 

Relevant academic research and scientific papers

Fluoride-assisted activation of calcium carbide: A simple method for the ethynylation of aldehydes and ketones

The fluoride-assisted ethynylation of ketones and aldehydes is described using commercially available calcium carbide with typically 5 mol % of TBAF·3H2O as the catalyst in DMSO. Activation of calcium carbide by fluoride is thought to generate an acetylide "ate"-complex that readily adds to carbonyl groups. Aliphatic aldehydes and ketones generally provide high yields, whereas aromatic carbonyls afford propargylic alcohols with moderate to good yields. The use of calcium carbide as a safe acetylide ion source along with economic amounts of TBAF·3H2O make this procedure a cheap and operationally simple method for the preparation of propargylic alcohols.

Ring expansions of 2-haloethynyl-2-norbornanols

2-Haloethynyl-2-norbornanols react with iodine and Koser's reagent in acetonitrile to afford two ring-expanded products, 2-[(Z)-haloiodomethylidene]bicyclo[3.2.1]octan-3-one and 3-[(Z)-haloiodomethylidene]bicyclo[3.2.1]octan-2-one. These results contrast with the 2-haloethynyl-2-bornanols which lead to the corresponding 3-octanones.