Fluorinated adamantane derivatives

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

Reexamination Certificate

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Reexamination Certificate

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11143978

ABSTRACT:
The present invention provides novel compounds which are useful for the production of fluorinated adamantane derivatives excellent in etching resistance and useful as photolithographic material and so on. Namely, the present invention provides compounds represented by the following formulae (3) and (4):in-line-formulae description="In-line Formulae" end="lead"?A(-G-Q-R)n  (3)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?Af(-Gf-Q-Rf)n  (4)in-line-formulae description="In-line Formulae" end="tail"?provided that the symbols in the formula have the following meanings:A: a n-valent group having n hydrogen atoms of adamantane converted to connecting bonds, wherein hydrogen atoms not converted to connecting bonds, may be each substituted by an alkyl group,R: a fluorinated monovalent organic group,n: an integer of from 1 to 4,G: —CH2— or a single bond,Q: —COO— or —OCO—,Af: a n-valent group (A) having n hydrogen atoms bonded to carbon atoms of adamantane converted to connecting bonds, wherein hydrogen atoms not converted to connecting bonds, may be each substituted by an alkyl group, in which at least one of hydrogen atoms forming C—H bonds is substituted by a fluorine atom,Rf: a fluorinated monovalent organic group,Gf: —CF2— or a single bond.

REFERENCES:
patent: 4284558 (1981-08-01), Barton et al.
patent: 7084295 (2006-08-01), Tanaka et al.
patent: 2005/0277785 (2005-12-01), Okazoe et al.
patent: 1064475 (1979-10-01), None
patent: 1 460 057 (2004-09-01), None
patent: 51-4102 (1976-01-01), None
patent: 57-79187 (1982-05-01), None
patent: 4-502319 (1992-04-01), None
patent: 9-43848 (1997-02-01), None
patent: 2001-60583 (2001-03-01), None
patent: 2003-280205 (2003-10-01), None
patent: 2004-123687 (2004-04-01), None
patent: 2005-23066 (2005-01-01), None
patent: 2005-89363 (2005-04-01), None
patent: WO 00/56694 (2000-09-01), None
patent: WO 03/055841 (2003-07-01), None
patent: WO 2004/050725 (2004-06-01), None
patent: WO 2004-052832 (2004-06-01), None
J.L.Adcock, H.Luo, and S.S.Zuberi Aerosol Flurination of 1-Chloroadamantane, 2-Chloroadamantane, and Methyl 1-Adamantylacetate: A Novel Synthetic Approach to 1- and 2-Substituted Hydroxyl-, Methyl-, and (Difluoromethyl)-F-adamantanes J.Org.Chem. 4749-4752, 57, 1992.
Färcasiu et al, J. Am. Chem. Soc., 1985, vol. 107, pp. 5717-5722.
Adcock et al, J. Org. Chem., 1996, vol. 61, pp. 5073-5076.
Adcock et al, J. Org. Chem., 1995, vol. 60, pp. 1099-2002.
Adcock et al, J. Org. Chem., 1995, vol. 57, pp. 4297-4300.
Helmut Duddeck, et al., “Synthesen und13C-NMR-spektroskopische Untersuchungen trifluormethylsubstituierter Adamantane”, Liebigs Ann. Chem., No. 3, 1985, pp. 545-554 (with English Abstract).
Douglas J. Raber, et al. “Structure Elucidation with Lanthanide-Induced Shifts 5. Evaluation of the Binding Ability of Various Functional Groups 1”; Monatshefte fur Chemi vol. 111, 43-52 (1980).
Database CA (Online); Chemical Abstracts Service, Columbus, Ohio, US; Kunihiko Kodama, et al. “Positive-working light-sensitive resist composition containing alkali-sensitive compound” XP002380188 and JP 2001 109156 A2 (Fuji Photo Film Co., Ltd., Japan) Apr. 20, 2001.
T. William Bentley, et al. “Weakly Nucleophilic Leaving Groups. Solvolyses of 1-Adamantyl and t-Butyl Heptafluorobutyrates and Trifluoracetates”; J. Chem. Soc. Perkin Trans. vol. ii (1989).
Database CA (Online); Chemical Abstracts Service, Columbus, Ohio, US; V.A. Soloshonok, et al. “Reaction fo 3,7- dimethylenebicyclo (3.3.1) nonane with pyridinium perfluorocarboxylates”; XP 002380189 and Database accession No. 1990:405759 abstract and Zhurnal Organicheskoi Khimii , 25(10), 2242-3 Coden; Zorkae; ISSN: 0514-7492, 1989.
Database CA (Online); Chemical Abstracts Service, Columbus, Ohio, US; D.T. Stoelting, et al, “Solvolysis of 1-(3-noradamantyl)-2-methylpropyl and 1-(3-noradamantyl)-2,2-dimethylpropyl pentamethylbenzenesulfonates” XP002380190 Database accession No. 1993: 147003 and Croatica Chemica Acta, 65(3) 517-38 Coden: CCACAA; ISSN: 001-1643, 1992.
Pavel A. Krasutsky, et al. “Observation of a Stable Carbocation in a Consecutive Criegee Rearrangement With Trifluoroperacetic Acid” J. Org. Chem. vol. 65, pp. 3926-3933, 2000.
Stephen R. Jones, et al. “Mechanism of Oxidation of Saturated Hydrocarbons by Lead(iv), Cobalt(iii), and Manganese(iii) Trifluoroacetates” J.C.S. Chem. Comm. 1976.
Pavel A. Krasutsky, et al. “Heterolytic decarboxylation involving acyltrifluoroacetyl peroxide intermediates” Tetrahedron Letter 43(48), pp. 8687-8691.
James L. Adcock, et al. Aerosol fluorination of 1-Chloroadamantane, 2-Chloroadamantane, 2-Chloroadamantane, and Methyl 1-Adamantylacetate: A Noval Synthetic Approach to 1-and 2-Substituted Hydryl-, Methyl-, and (Difluoromethyl)- F- Adamantanes; Journal of Organic Chemistry, 57(17), pp. 4749-4752, 1992.
James L. Adcock, et al. “Polarized C-H Groups as Novel Hydrotgen-Bond Donors in Hydryl-F-alkyl Esters: Unequivocal Examples fo rthe Pinchas Effect” Journal of Organic Chemistry, 60(7), pp. 1999-2002 (1995).
Oldrich Paleta, et al. “Synthesis of 1-Adamantanol 2,3,3-Trifluoroacrylate” Journal of Fluorine chemistry 47(3) pp. 435-440, (1990).
Klaus Banert, et al. “Nucleophile Substitution bei 4,4-Dimethyl-2-adamantyl- Substraten: Ruckseitenangriff bei 2-Adamantan-Derivaten” Chemische Berichte, vol. 119(12), pp. 3826-3841, (1986).
Neil A. Marron, et al. “A Direct Photochemical Synthesis of 1,2-Disubstituted Adamantanes” Synthetic Communications, vol. 7(8), pp. 515-520 (1977).
Muthiah Manoharan, et al., “Lipidic Nucleic Acids” Tetrahedron Letters, vol. 36, No. 21, 1995, pp. 3651-3654.
U.S. Appl. No. 11/611,183, filed Dec. 15, 2006, Oharu et al.
U.S. Appl. No. 11/567,391, filed Dec. 6, 2006, Wang et al.

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