Title:
ADAMANTANEMETHANOL DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF
Document Type and Number:
WIPO Patent Application WO/1999/054271
Kind Code:
A1
Abstract:
Adamantanemethanol derivatives represented by general formula (1) wherein R?a¿ is hydrogen or a hydrocarbon group; R?b¿ is a hydrocarbon group having, at the binding site to the adjacent carbon atom, a carbon atom bearing at least one hydrogen atom bonded thereto; and R?c¿, R?d¿ and R?e¿ are each hydrogen, optionally protected hydroxyl or the like, with the provisos that when R?a¿ is hydrogen or methyl and R?b¿ is methyl, at least one of the carbon atoms constituting the adamantane skeleton has protected hydroxyl or the like in a state bonded thereto and that when one of R?a¿ and R?b¿ is methyl and the other is ethyl, the adamantane ring has at least one more substituent in addition to the HO-C(R?a¿)(R?b¿)- group represented in the general formula (1).
Inventors:
NAKANO TATSUYA (JP)
SHIMOJITOSYO HIROSHI (JP)
SHIMOJITOSYO HIROSHI (JP)
Application Number:
PCT/JP1999/002110
Publication Date:
October 28, 1999
Filing Date:
April 21, 1999
Export Citation:
Assignee:
DAICEL CHEM (JP)
NAKANO TATSUYA (JP)
SHIMOJITOSYO HIROSHI (JP)
NAKANO TATSUYA (JP)
SHIMOJITOSYO HIROSHI (JP)
International Classes:
C07C31/137; C07C31/27; C07C43/315; (IPC1-7): C07C31/137; C07C31/27; C07C35/37; C07C29/143; C07C29/147; C07C43/196; C07C41/26
Foreign References:
| EP0043298A1 | 1982-01-06 | |||
| EP0990634A1 | 2000-04-05 | |||
| EP0055654A1 | 1982-07-07 | |||
| EP1000924A1 | 2000-05-17 |
Other References:
HEAGY M D, ET AL.: "PREPARATION AND 13C NMR SPECTROSCOPIC STUDY OF DISUBSTITUTED ADAMANTANE-1,3-DIMETHYLDIYL DICATIONS", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 60, no. 22, 1 January 1995 (1995-01-01), US, pages 7351 - 7354, XP002919732, ISSN: 0022-3263, DOI: 10.1021/jo00127a049
KOVALEV V V, ET AL.: "REACTION OF 1-ADAMANTANOL WITH ALPHA-OLEFINS IN TRIFLUOROACETIC ACID", ZHURNAL ORGANICHESKOI KHIMII, MAIK NAUKA, MOSCOW, RU, vol. XVII, no. 01, 1 January 1981 (1981-01-01), MOSCOW, RU, pages 109 - 116, XP002919733, ISSN: 0514-7492
LOMAS J S, THORNE M P: "STRUCTURE AND ISOTOPE EFFECTS UPON THE THERMAL DECOMPOSITION OF CARBAMATES OF HIGHLY CONGESTED TERTIARY ALCOHOLS", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL SOCIETY, LETCHWORTH; GB, vol. 02, no. 02, 1 January 1982 (1982-01-01), LETCHWORTH; GB, pages 221 - 226, XP002919734, ISSN: 0368-1769
OLAH G A, ET AL.: "SOLVOLYTIC AND STABLE ION STUDIES OF 1,1'-DIADAMANTYLMETHYL CATIONS", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 70, 1 January 1982 (1982-01-01), US, pages 1040 - 1047, XP002919735, ISSN: 0022-3263, DOI: 10.1021/jo00345a029
LOMAS J S, LUONG P K, DUBOIS J-E: "ACID-CATALYZED DEHYDRATION AND ACETOLYSIS OF TERTIARY METHYL-AND TERT-BUTYLCARBINOLS. EMPIRICAL FORCE FIELD TREATMENT OF TERT-BUTYL/METHYL REACTIVITY RATIOS IN SOLVOLYSIS REACTIONS OF ALCOLHOLS AND P-NITROBENZOATES", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 44, no. 10, 1 January 1979 (1979-01-01), US, pages 1647 - 1654, XP002919736, ISSN: 0022-3263, DOI: 10.1021/jo01324a015
EDWARDS G J, JONES S R, MELLOR J M: "ANODIC OXIDATION OF SUBSTITUTED ADAMANTANES", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL SOCIETY, LETCHWORTH; GB, vol. 02, no. 04, 1 January 1977 (1977-01-01), LETCHWORTH; GB, pages 505 - 510, XP002919737, ISSN: 0368-1769
MOLLE, GERARD ET AL., TETRAHEDRON, vol. 40, no. 24, 1984, pages 5113 - 19
KRAUS, GEORGE A., JOURNAL OF ORGANIC CHEMISTRY, vol. 59, no. 4, pages 922 - 3
DUA, SURESH: "Journal of Chemical Society, Perkin Transactions 2", PHYSICAL ORGANIC CHEMISTRY, vol. 6, pages 1443 - 48
LANDA, S.: "Collection of Czechoslovak Chemical Communications", vol. 24, 1959, ACADEMIC PRESS, pages: 1320 - 26
HEAGY MICHAEL D., JOURNAL OF ORGANIC CHEMISTRY, vol. 60, no. 22, 1995, pages 735154
KOVAEV V. V., ZH. ORG. KHIM., vol. 17, no. 1, 1981, pages 109 - 16
LOMAS, JOHN S., JOURNAL OF CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2, 1982, pages 221 - 26
OLAH, GEORGE A., JOURNAL OF ORGANIC CHEMISTRY, vol. 6, no. 47, pages 1040 - 47
LOMAS, JOHN S., JOURNAL OF ORGANIC CHEMISTRY, vol. 44, no. 10, 1979, pages 1647 - 54
FISCHER, WALTER, HELVETICA CHIMICA ACTA., vol. 59, no. 6, 1976, pages 1953 - 62
See also references of EP 0990632A4
KOVALEV V V, ET AL.: "REACTION OF 1-ADAMANTANOL WITH ALPHA-OLEFINS IN TRIFLUOROACETIC ACID", ZHURNAL ORGANICHESKOI KHIMII, MAIK NAUKA, MOSCOW, RU, vol. XVII, no. 01, 1 January 1981 (1981-01-01), MOSCOW, RU, pages 109 - 116, XP002919733, ISSN: 0514-7492
LOMAS J S, THORNE M P: "STRUCTURE AND ISOTOPE EFFECTS UPON THE THERMAL DECOMPOSITION OF CARBAMATES OF HIGHLY CONGESTED TERTIARY ALCOHOLS", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL SOCIETY, LETCHWORTH; GB, vol. 02, no. 02, 1 January 1982 (1982-01-01), LETCHWORTH; GB, pages 221 - 226, XP002919734, ISSN: 0368-1769
OLAH G A, ET AL.: "SOLVOLYTIC AND STABLE ION STUDIES OF 1,1'-DIADAMANTYLMETHYL CATIONS", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 70, 1 January 1982 (1982-01-01), US, pages 1040 - 1047, XP002919735, ISSN: 0022-3263, DOI: 10.1021/jo00345a029
LOMAS J S, LUONG P K, DUBOIS J-E: "ACID-CATALYZED DEHYDRATION AND ACETOLYSIS OF TERTIARY METHYL-AND TERT-BUTYLCARBINOLS. EMPIRICAL FORCE FIELD TREATMENT OF TERT-BUTYL/METHYL REACTIVITY RATIOS IN SOLVOLYSIS REACTIONS OF ALCOLHOLS AND P-NITROBENZOATES", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 44, no. 10, 1 January 1979 (1979-01-01), US, pages 1647 - 1654, XP002919736, ISSN: 0022-3263, DOI: 10.1021/jo01324a015
EDWARDS G J, JONES S R, MELLOR J M: "ANODIC OXIDATION OF SUBSTITUTED ADAMANTANES", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL SOCIETY, LETCHWORTH; GB, vol. 02, no. 04, 1 January 1977 (1977-01-01), LETCHWORTH; GB, pages 505 - 510, XP002919737, ISSN: 0368-1769
MOLLE, GERARD ET AL., TETRAHEDRON, vol. 40, no. 24, 1984, pages 5113 - 19
KRAUS, GEORGE A., JOURNAL OF ORGANIC CHEMISTRY, vol. 59, no. 4, pages 922 - 3
DUA, SURESH: "Journal of Chemical Society, Perkin Transactions 2", PHYSICAL ORGANIC CHEMISTRY, vol. 6, pages 1443 - 48
LANDA, S.: "Collection of Czechoslovak Chemical Communications", vol. 24, 1959, ACADEMIC PRESS, pages: 1320 - 26
HEAGY MICHAEL D., JOURNAL OF ORGANIC CHEMISTRY, vol. 60, no. 22, 1995, pages 735154
KOVAEV V. V., ZH. ORG. KHIM., vol. 17, no. 1, 1981, pages 109 - 16
LOMAS, JOHN S., JOURNAL OF CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2, 1982, pages 221 - 26
OLAH, GEORGE A., JOURNAL OF ORGANIC CHEMISTRY, vol. 6, no. 47, pages 1040 - 47
LOMAS, JOHN S., JOURNAL OF ORGANIC CHEMISTRY, vol. 44, no. 10, 1979, pages 1647 - 54
FISCHER, WALTER, HELVETICA CHIMICA ACTA., vol. 59, no. 6, 1976, pages 1953 - 62
See also references of EP 0990632A4
Attorney, Agent or Firm:
Goto, Yukihisa (Higashitenma 2-chome Kita-ku Osaka-shi Osaka, Higashitenma 2-chome Kita-ku Osaka-shi Osaka, JP)
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