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Upstream product

• 7417-18-7 2-methoxyphenethyl alcohol 
• 93-25-4 2-methoxyphenylacetic acid 
• 36449-75-9 1-(2-bromoethyl)-2-methoxybenzene 
• 78-94-4 methyl vinyl ketone 
• 63449-79-6 4-(o-methoxyphenyl)-butan-2-one 
• 1826-67-1 vinyl magnesium bromide 

Relevant academic research and scientific papers

Intramolecular hydrogen bond effect in meta-cycloaddition of arene to olefin

The intramolecular meta-photocycloaddition of bichromophores 1a and 1b is examined and the observed stereochemistry of cycloaddition is rationalized in terms of hydrogen bond effect introduced by the 3-hydroxy group in the 5-phenylpent-1-ene skeleton.

Diastereoselective intramolecular meta photocycloaddition of side-chain- substituted 5-(2-methoxyphenyl)pent-1-enes

Irradiation of a series of 5-(2-methoxyphenyl)pent-1-enes substituted with a hydroxy or trimethylsilyloxy group at the α-, β-, or γ-position of the side-chain yields in all cases meta photocycloadducts, in which the configuration at the substituted carbon atom is mainly endo. This indicates that the diastereoselectivity originates from minimization of steric interactions between the side-chain substituent and the ortho-methoxy group at the arene unit. Hydrogen bonding does not seem to be involved. The introduction of the side-chain substituents also influences the regioselectivity of the addition: The linear to angular adduct ratios are significantly increased compared to the case of the parent compound.