Fluorinated adamantane and its derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic halides

Reexamination Certificate

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Reexamination Certificate

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07488847

ABSTRACT:
The present invention provides a process A1 for producing a compound (5A), which comprises fluorinating a compound (3A-1) by liquid phase fluorination to a compound (4A-1), followed by a decomposition reaction of an ester bond; a process A2 for producing a compound (5A), which comprises fluorinating a compound (3A-2) by liquid phase fluorination to a compound (4A-2), followed by a decomposition reaction of an ester bond; and a process B for producing a compound (5B), which comprises fluorinating a compound (3B) by liquid phase fluorination to a compound (4B), followed by hydrolysis or alcoholysis. Further, the present invention provides a compound (5A) wherein n is 2 to 4, and a compound (5B) wherein n is 3 or 4.in-line-formulae description="In-line Formulae" end="lead"?A(—CH2—OCO—R)n  (3A-1)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?Af(—CF2—OCO—Rf)n  (4A-1)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?A(—COOR)n  (3A-2)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?Af(—COORf)n  (4A-2)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?Af(—COF)n  (5A)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?A(—OCO—R)n  (3B)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?Af(—OCO—Rf)n  (4B)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?Af(—OH)n  (5B)in-line-formulae description="In-line Formulae" end="tail"?provided that the carbon atom in adamantane to which —OCO—Rfis bonded, is a tertiary carbon atom, A is a n-valent group having n hydrogen atoms in adamantane converted to connecting bonds, R is a fluorinated monovalent organic group, n is an integer of from 1 to 4, Afis a group having at least one of hydrogen atoms in the group A substituted by a fluorine atom, and Rfis a fluorinated monovalent organic group.

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