Adamantane derivative and process for producing the same
View Patent ↗Provided is an adamantane derivative represented by Formula (I) or (II): wherein X represents a halogen atom; Y represents an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a halogen atom or a hetero atom-containing group; R 1 to R 4 represent independently hydrogen, a halogen atom, an alkyl group having 1 to 10 carbon atoms or a halogenated alkyl group having 1 to 10 carbon atoms; m represents an integer of 0 to 15, and n represents an integer of 0 to 10; and excluded is a case where in Formula (I), m and n are 0 at the same time and R 3 and R 4 are a hydrogen atom at the same time. Capable of being provided is a novel adamantane derivative which is useful as a modifying agent for a resin for a photoresist and a dry etching resistance-improving agent in the photolithography field, agricultural and medical intermediates and other various industrial products.
1. A substituted adamantane of Formula (I) or (II):
wherein
X represents a halogen atom;
Y is a C 1 -C 10 alkyl group, a halogenated C 1 -C 10 alkyl group, a halogen atom or a hetero atom-containing group;
R 1 and R 2 represents, independently, hydrogen, a halogen atom, a C 1 -C 10 alkyl group or a halogenated C 1 -C 10 alkyl group;
R 3 and R 4 represent, independently, hydrogen, a C 1 -C 10 alkyl group, or a C 1 -C 10 halogenated alkyl group,
wherein R 3 and R 4 cannot both be hydrogen in Formula (I);
wherein, in the formula (I), m represents an integer of 0 to 15, and n represents an integer of 1 to 10;
wherein, in the Formula (II), m represents an integer of 1 to 15.
2. A substituted adamantane selected from the group consisting of
wherein
X represents a halogen atom;
Y is a C 1 -C 10 alkyl group, a halogenated C 1 -C 10 alkyl group, a halogen atom or a hetero atom-containing group;
R 1 and R 2 represent, independently, hydrogen, a halogen atom, a C 1 -C 10 alkyl group or a halogenated C 1 -C 10 alkyl group;
R 3 and R 4 represent, independently, hydrogen, a C 1 -C 10 alkyl group, or a C 1 -C 10 halogenated alkyl group,
wherein R 3 and R 4 cannot both be hydrogen in Formulae (Ia-If);
wherein, in the formulae (Ia-If), m represents an integer of 0 to 13, and n represents an integer of 1 to 10;
wherein, in the Formula (IIa-IIe), m represents an integer of 1 to 13.
3. A process for producing the substituted adamantane of claim 1 , comprising
reacting an alcohol comprising an adamantyl group represented by Formula (III) or (IV):
wherein in Formula (III), n represents an integer of 1 to 10;
with a carbonyl compound represented by Formula (V):
and at least one hydrogen halide gas; wherein R 3 and R 4 in Formula (V) are not both hydrogen when the carbonyl compound of formula (V) is reacted with the adamantyl group of Formula (III), and wherein m represents an integer of 1 to 13.