13084-56-5

Usage

InChI:InChI=1/C9H10/c1-2-4-6-3(1)7-5(2)9(7)8(4)6/h2-9H,1H2

Upstream product

• 452-61-9 pentacyclo<4.3.0.0^2,5.0^3.8.0^4,7>nonane 
• 15844-05-0 Pentacyclo<4.3.0.0^2,5.0^3,8.0^4,7>nonane-4-carboxylic acid 
• 7785-10-6 tetracyclo<4.3.0.0.^2,4.0^3,7>non-8-ene 
• 35589-16-3 4-Chloropentacyclo<4.3.0.0^2,5.0^3,8.0^4,7>nonane 
• 15291-18-6 Pentacyclo<4.3.0.0^2,5.0^3,8.0^4,7>nonan-9-one 
• 13084-57-6 Tetracyclo<4.3.0.0^2,4.0^3,7>nonan-8-on-p-toluolsulfonylhydrazon 

Downstream Products

• 1521-75-1 brendane 
• 19026-97-2 twistbrendane 
• 56555-19-2 Tetracylo<4.3.0.0^3,9.0^4,7>nonan 

Relevant academic research and scientific papers

The 13C and 1H N.M.R. Spectra of Homocubane, Norsnoutane and their 9-Keto- and 9,9-Ethylenedioxy-derivatives, and a Novel Route to Functionalised Brendanes

The 13C and 1H n.m.r. spectra of homocubane (pentacyclo2,5.03,8.04,7>nonane) (5), norsnoutane (pentacyclo2,4.03,8.05,7>nonane) (12) and their 9-keto- and 9,9-ethylenedioxy-derivatives have been analysed using deuterium labelling.The protons α to the carbonyl and acetal group and the carbon atoms bearing these protons shown unusual absorptions.The substituent effects in homocubanes and norbornanes are similar and no significant additional effect is apparent in the cage structure; the effect of the endo-annulated cyclopropane rings in the norsnoutanes is discussed.The hydrochloric acid-catalysed rearrangement of 9,9-ethylenedioxypentacyclo2,4.03,8.05,7>nonane (10) gives the brendane derivative, exo-2-chlorotricyclo3,7>non-4-en-8-one (16).

Generation and reactions of pentacyclo[4.3.0.02,4.0 3,8.05,7]non-4-ene

(Chemical Equation Presented) The highly pyramidalized alkene, pentacyclo[4.3.0.02,4.03.8.05,7]non-4-ene (9), has been generated via treatment of 4,5-diiodopentacyclo[4.3.0.0 2.4.03,8.05,7]

Hydrogenolysis of Small Cycloalkanes, XIII - Hydrogenation of Homucubane Derivatives

Two dihydro products 5a and 7a are formed by hydrogenation of homocubane (6a) with Pd-, Pt-, and Rh-catalysts.Only the unsymmetric 7a reacts further to give twistbrendane (8a).In addition, ca. 20percent brendane (11a) is obtained by hydrogenation of homocuneane (9a), which is formed from 6a by rearrangement on the catalyst.The yield of the symmetric dihydro product 5b is raised up to 40percent in the case of hydrogenation of the ethylene acetal 6b of the 9-ketone on Rh/Al2O3.With the ester 6d no 5d is obtained but 7d and 8d only.