73151-74-3

Basic information

• Product Name: 1,3-methanonaphthalene-4-yl methyl ether
• Synonyms: 1,3-methanonaphthalene-4-yl methyl ether
• CAS NO: 73151-74-3
• Molecular Weight: 174.243
• Mol File: 73151-74-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,3-methanonaphthalene-4-yl methyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-methanonaphthalene-4-yl methyl ether(73151-74-3)
• EPA Substance Registry System: 1,3-methanonaphthalene-4-yl methyl ether(73151-74-3)

Safety Data

• Hazardous Substances Data: 73151-74-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 7605-04-1 exo-2-benzonorbornenyl chloride 
• 7605-04-1 exo-2-benzonorbornyl chloride 
• 7605-05-2 endo-2-benzonorbornenyl chloride 

Relevant articles and documents

Intramolecular Aryl-Assisted Photolytic Cleavage of 2-Benzonorbornenyl Derivatives. A High Excited-State Exo/Endo Reactivity Ratio and a Novel Wagner-Meerwein Rearrangement

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Photolytic Cleavage of Remote Functional Groups in Polyfunctional Molecules. Photolysis of exo- and endo-2-Benzonorbornenyl Chlorides and Methanesulfonates

The photochemistry and photophysics of the title compounds are reported.The exo chloride exhibits a facile cleavage of the C - Cl bond upon excitation of the aryl chromophore (eq 1 - 3).The reaction has a rate > 700-fold larger than that observed with the endo isomer, derives from the singlet excited state, and leads to the formation of "hot" carbocations as well as free radicals.The exo mesylate shows similar characteristics (eq 4).A mechanism (Scheme II) is suggested which incorporates both heterolytic fission as well as sequential homolytic fission (to a polarized radical pair), followed by electron transfer to form an ion pair.The stereoelectronically controlled activation of the C - Cl and C - OMs moieties is explaned by a correlation diagram (Figure 5) which depicts the ?,?* state as correlating with the diradical product state through an avoided crossing with the C - X ?,?* state.Calculations indicate that this avoided crossing is considerably larger (and the barrier to reaction therefore considerably smaller) when the C - X unit in the 2-benzonorbornenyl series is exo.