Heavy-hydrogenated norbornyl (meth)acrylates, process for producing them, polymers thereof and optical members
View Patent ↗A novel compound represented by a formula [1] wherein R 1 and R 2 respectively represent a light or heavy hydrogen atom, R 3 represents a light or heavy hydrogen atom or a methyl group in which tree hydrogen atoms are respectively light or heavy hydrogen atoms, and R 4 is a norbornyl group provided that four or more hydrogen atoms in the norbornyl group are heavy hydrogen atoms; and a novel polymer produced by polymerization of a composition comprising the compound are disclosed.
1. A process for producing a compound represented by a formula [1]:
wherein R 1 and R 2 respectively represent a light or heavy hydrogen atom, R 3 represents a light or heavy hydrogen atom or a methyl group in which three hydrogen atoms are respectively light or heavy hydrogen atoms, and R 4 is a norbornyl group provided that four or more hydrogen atoms in the norbornyl group are heavy hydrogen atoms, comprising:
(i) reacting a norborneol with heavy water in the presence of palladium catalyst under an atmosphere of light hydrogen gas, or
(ii) reacting a norbornanone with heavy water in the presence of palladium catalyst under an atmosphere of light hydrogen gas and then reducing the obtained deuterated norbornanone,
thereby to obtain a deuterated norborneol containing four or more heavy hydrogen atoms in its norbornyl group; and
reacting said deuterated norborneol with a compound represented by a formula [2]:
wherein R 1 and R 2 respectively represent a light or heavy hydrogen atom, R 3 represents a light or heavy hydrogen atom or a methyl group in which three hydrogen atoms are respectively light or heavy hydrogen atoms, and X represents a halogen atom, a hydroxyl group or an alkoxy group.
2. A process for producing a deuterated norborneol comprising:
(i) reacting a norborneol with heavy water in the presence of palladium catalyst under an atmosphere of light hydrogen gas, or
(ii) reacting a norbornanone with heavy water in the presence of palladium catalyst under an atmosphere of light hydrogen gas and then reducing the obtained deuterated norbornanone.