56180-57-5

Upstream product

• 16205-87-1 2-trimethylsilylbicyclo<2.2.1>hept-2-ene 
• 98-88-4 benzoyl chloride 
• 36144-50-0 phenyl-(6-phenyl-1,2,3,4,7,8,9,10,10a,10b-decahydro-1,4;7,10-dimethano-benzo[c]chromen-4a-yl)-methanone 
• 497-38-1 Norbornan-2-on 
• 98-07-7 Benzotrichlorid 
• 860372-45-8 (3-chloro-[2]norbornyl)-phenyl ketone 

Relevant academic research and scientific papers

Friedel-Crafts acylation of 2-trimethylsilylnorbornene. Effect of acyl group on the position of attack

The acylation of 2-trimethylsilylnorbornene 1 in the presence of aluminium chloride gives minor quantities of the expected 2-norbornenyl ketones 4. The formation of 3 and 5 as major products indicates that either α- or β-attack takes place predominantly depending on the nature of the acyl group, and the β-silicon effect is not a decisive factor. The β-silyl cation intermediate 2 mainly leads to nortricyclyl ketones 3 through 1,3- deprotonation, and the α-silyl cation 8 undergoes rearrangement to give novel bridge-head silylated products 5.

Cathodic Addition of Benzylidyne Trichloride to Ketones and Aldehydes

Ketones are converted to homologated enones 7a-g in good yields by cathodic addition of benzylidyne trichloride (1d).As intermediates α-Chlorooxiranes 6 are assumed, which rearrange via α-keto carbenium ions 9 to enones.The intermediacy of 9 is supported by the addition of 1d to norcamphor, where the products indicate equilibrating norbornyl cations as intermediates. α,β-Unsaturated ketones lead depending on steric shielding of the double bond to the cyclopropane 23 as 1,4-adduct or the enone 26 as 1,2-adduct.With aldehydes and 1d, α-chloro or βhydroxy ketones, the conversion products of 2-chlorooxiranes, are obtained.