56206-38-3

Basic information

• Product Name: 5-methoxybicyclo[2.2.2]oct-2-ene
• Synonyms: Bicyclo(2.2.2)oct-2-ene, 5-methoxy-
• CAS NO: 56206-38-3
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.2069
• Mol File: 56206-38-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 177.3°C at 760 mmHg
• Flash Point: 52.4°C
• Density: 0.97g/cm³
• Vapor Pressure: 1.41mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: 5-methoxybicyclo[2.2.2]oct-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methoxybicyclo[2.2.2]oct-2-ene(56206-38-3)
• EPA Substance Registry System: 5-methoxybicyclo[2.2.2]oct-2-ene(56206-38-3)

Safety Data

• Hazardous Substances Data: 56206-38-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 3635-95-8 exo-tricyclo<3.2.1.0^2,4>oct-6-ene 
• 500-23-2 bicyclo[2.2.2]octa-2,5-diene 
• 61640-88-8 C₁₄H₁₆N₂O₂S 
• 74-88-4 methyl iodide 
• 6688-07-9 hydroxy-5 exo bicyclo<2.2.2>octene-2 
• 121654-21-5 6-exo-methoxytricyclo<3.2.1.0^2,7>octane 

Relevant articles and documents

Effect of a methoxy substituent on the vinylcyclobutane carbon migration

(Chemical Equation Presented) Over the temperature range 250-300°C, 8-exo-methoxybicyclo[4.2.0]oct-2-ene (1a) undergoes a [1,3] sigmatropic rearrangement to 5-exo- and 5-endo-methoxybicyclo[2.2.2]oct-2-enes, 2a and 2b, respectively, with a clear preference for the si product: si/sr = 3.2. Both 1a and its 8-endo epimer 1b experience appreciable epimerization and fragmentation. A long-lived intermediate with weakly interacting diradical centers, one of which is stabilized by a methoxy substituent, can account for all such observations.

Corner Attack on endo- and exo-Tricyclo2,4>oct-6-ene by Deuterium and Mercuric Ions: The Effect of Electrophile on Reaction Course

Reaction of endo-tricyclo2,4>oct-6-ene (1) with mercuric acetate in methanol gave 2b as the major product of reaction after stereospecific reduction with sodium-mercury amalgam in sodium deuteroxide, along with 3b and 4b.In contrast 4-endo-deuterio-2-endo-methoxybicyclooct-6-ene (2b) is formed as a minor product from acid-catalyzed reaction of endo-tricyclo2,4>oct-6-ene (1) with methanol-d1.Methoxymercuration of exo-tricyclo2,4>oct-6-ene (8) occurs at the double bond to give 7-exo-(acetoxymercurio)-6-exo-methoxy-exo-tricyclo2,4>octane (9c; 89percent).Acid-catalyzed addition of methanol to exo-tricyclo2,4>oct-6-ene (8) gave 6-exo-methoxy-exo-tricyclo2,4>octane (9a; 15percent) and 6-exo-methoxytricyclo2,7>octane (11) in a process involving corner attack of the electrophile.This tricyclic compound rearranges to 5-exo-methoxybicyclooct-2-ene (10a; 55percent).The preference for corner attack by mercuric ion and deuteron with C2-C4 bond cleavage in the reactions of 1 and 8 is rationalized and the competition between reaction at cyclopropane and addition to the double bond discussed.