4685-74-9

Usage

InChI:InChI=1/C14H20/c1-2-4-6-8-14-11-9-13(10-12-14)7-5-3-1/h9-12H,1-8H2

Upstream product

• 89507-11-9 3,6-Bis(ethylendithioacetal) 
• 62985-49-3 3-methylenespiro<5.7>trideca-1,4-diene 
• 116059-93-9 dispiro<2.2.6.2>tetradeca-4,13-diene 
• 89507-01-7 3,6-Bis(tosyloxy)<8>paracyclophan 

Downstream Products

• 7048-98-8 <8>Metacyclophane 
• 89507-00-6 2-(<8>Metacyclophan-12-ylcarbonyl)benzoesaeure 
• 3454-07-7 1-ethenyl-4-ethyl-benzene 
• 62985-48-2 1-propyl-4-vinylbenzene 
• 106750-47-4 6,7,8,9,10,11-hexahydro-2-methyl-5H-benzocyclononene 
• 7125-05-5 Benzocyclodecen 
• 89506-95-6 1-Brom-8-(4-bromphenyl)octan 
• 89506-94-5 10-Brom<8>metacyclophan 
• 89506-98-9 10,12-Dibrom<8>metacyclophan 
• 89506-96-7 10,11,12-Tribrom<8>metacyclophan 
• 89506-97-8 1-Brom-8-(2,4,5-tribromphenyl)octan 

Relevant academic research and scientific papers

FLASH VACUUM THERMOLYSIS OF DISPIROALKADIENES

The Flash Vacuum Thermolysis (FVT) of dispirotetradeca -4,13-diene (7a). dispirotrideca-4,12-diene (7b) and dispirodeca-4,9-diene (7e) at 500-750 deg C is reported.The complicated reaction mixture from 7a and 7b (Scheme 3) included at lower temperatures vinylspiroalkadienes 9, ethylidenespiroalkadiene 10b, β-ethylcycloalkabenzenes 11, while at higher temperatures, p-n-alkyl-(5) and p-sec-alkylstyrenes 14 and p-divinylbenzene (15) dominated.Product formation is explained by invoking diradicals 8,6 and 12 as well as the cyclophanes 1 and 13 as intermediates.For 7e, the product mixture was less complicated and consisted of p-ethylstyrene (5e), 15 and, unexpectedly,p-isopropylstyrene (14e) which contains one carbon more than the starting material.The analysis and interpretation of product formation largely confirms previously suggested reaction pathways and furnishes further interesting details.However, new and unexpected features are also encountered, especially in the fragmentations of 1 and 13 which may stimulate future investigations on the thermal behaviour of these relatively simple hydrocarbons.

SCOPE AND LIMITATIONS OF THE FLASH VACUUM THERMOLYSIS APPROACH TO SMALL PARACYCLOPHANES

Flash vacuum thermolysis (FVT) of 3-methylene-6-spirocyclohexa-1,4-dienes (2) was investigated as a synthetic approach to small paracyclophanes 1 (1a, n=8; 1b, n=7; 1c, n=6).The method was found to be preparatively attractive for 1a (80percent yield), less so for 1b (7percent useful yield), and not at all for 1c which was too unstable to survive the conditions of its formation.Besides 1, p-alkylstyrenes (3) and 2-methylbenzocycloalkenes (4) were obtained; the total recovery of monomeric products was good (60-85percent).The temperature dependence of product formation furnished useful information on the mechanisms of formation and decomposition of 1 under the conditions of FVT.

Cyclophanes, XXII. The Chemical Behavior of Paracyclophane: Reactions of the Polymethylene Bridge

The chemical behavior of paracyclophanes functionalized in the polymethylene bridge has been investigated.The reaction of trans-paracyclophan-4-ene (3) with dichloro- and dibromocarbene provides under exclusive attack of the bridge double bond the a