Title:
NOVEL COMPOUNDS COMPRISING A THIOCARBONYL-SULFANYL GROUP, WHICH CAN BE USED FOR THE RADICAL SYNTHESIS OF ALPHA-PERFLUOROALKYLAMINES
Document Type and Number:
WIPO Patent Application WO2004024681
Kind Code:
A3
Abstract:
The invention relates to compounds having general formula (I), the preparation method thereof and the use of same in radical organic synthesis. The invention also relates to compounds having formula (II), the preparation method thereof and a method of preparing compounds having formula (VIII).
Inventors:
ZARD SAMIR (FR)
GAGOSZ FABIEN (FR)
TOURNIER LUCIE (FR)
GAGOSZ FABIEN (FR)
TOURNIER LUCIE (FR)
Application Number:
PCT/FR2003/002697
Publication Date:
July 01, 2004
Filing Date:
September 11, 2003
Export Citation:
Assignee:
RHODIA CHIMIE SA (FR)
ZARD SAMIR (FR)
GAGOSZ FABIEN (FR)
TOURNIER LUCIE (FR)
ZARD SAMIR (FR)
GAGOSZ FABIEN (FR)
TOURNIER LUCIE (FR)
International Classes:
C07C67/293; C07C67/297; C07C69/63; C07C69/78; C07C231/12; C07C233/13; C07C233/18; C07C233/36; C07C233/69; C07C233/78; C07C327/36; C07C329/16; C07C329/18; C07D207/27; C07D209/12; C07D209/14; C07D209/48; C07D317/36; C07D339/06; C07F7/08; C07F9/40; C07C233/31; C07D207/26; (IPC1-7): C07C327/36; C07D317/36; C07F7/08; C07D209/48; C07F9/40; C07D207/26; C07C233/18; C07D209/14; C07C231/12; C07C233/13
Other References:
Q.-Y. CHEN, ET AL.: "Perfluoro- and polyfluorosulphonic acids. 21. Synthesis of difluoromethyl esters using fluorosulphonyldifluoroacetic acid as a difluororcarbene precursor", JOURNAL OF ORGANIC CHEMISTRY, vol. 54, no. 13, 23 June 1989 (1989-06-23), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 3023 - 3027, XP002274706, ISSN: 0022-3263
F. GAGOSZ, ET AL.: "A direct approach to alpha-trifluoroamines", ORGANIC LETTERS, vol. 5, no. 15, 1 July 2003 (2003-07-01), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 2655 - 2657, XP002274506, ISSN: 1523-7060
P. DELDUC, ET AL.: "A convenient source of alkyl and acyl radicals", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 4, 15 February 1988 (1988-02-15), ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH., GB, pages 308 - 310, XP002274695, ISSN: 0022-4936
J. BOIVIN, ET AL.: "A flexible, convergent approach to piperidines, pyridines, azepines, and related derivatives", TETRAHEDRON LETTERS, vol. 40, no. 19, 7 May 1999 (1999-05-07), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 3701 - 3704, XP004163809, ISSN: 0040-4039
A. LIARD, ET AL.: "A new synthesis of alpha-tetralones", TETRAHEDRON LETTERS, vol. 38, no. 10, 10 March 1997 (1997-03-10), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 1759 - 1762, XP004054986, ISSN: 0040-4039
B. QUICLET-SIRE, ET AL.: "An unusual route to deoxysugars by hydrogen atom transfer from cyclohexane. Possible manifestation of polar effects in a radical process", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 118, no. 38, 25 September 1996 (1996-09-25), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 9190 - 9191, XP002244969, ISSN: 0002-7863
A. LIARD, ET AL.: "A practical method for the reductive cleavage of the sulfide bond in xanthates", TETRAHEDRON LETTERS, vol. 37, no. 33, 12 August 1996 (1996-08-12), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 5877 - 5880, XP004030563, ISSN: 0040-4039
T. NAKAI, ET AL.: "Potential synthetic utility of [3,3]-sigmatropic rearrangement of S-allyl dithiocarbamates. New routes to alpha,beta-unsaturated aldehydes", TETRAHEDRON LETTERS, no. 41, October 1974 (1974-10-01), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 3625 - 3628, XP002244970, ISSN: 0040-4039
DATABASE CHEMABS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002274701, retrieved from STN Database accession no. 2003:396832
T. HIRAO, ET AL.: "Catalytic pinacol coupling in the presence of acylating agent", SYNLETT, no. 11, November 2000 (2000-11-01), THIEME VERLAG, STUTTGART, DE, pages 1658 - 1660, XP002274696, ISSN: 0936-5214, Retrieved from the Internet
C.M. HU, ET AL.: "Synthesis of functionalised organic molecules containing a tetrafluoroethylene fragment by cobaloxime-promoted fluoroalkylation with substituted tetrafluoroethyl bromides", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 3, 7 February 1993 (1993-02-07), ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH, GB, pages 331 - 334, XP002274697
J. MÖNIG, ET AL.: "One-electron reduction of halothane (2-bromo-2-chloro-1,1,1-trifluoroethane) by free radicals. Radiation chemical model system for reductive metabolism", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS II, no. 12, 1984, ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH, GB, pages 2057 - 2063, XP002274698, ISSN: 0300-9580
S.H. BROWN, ET AL.: "Making mercury-photosensitised dehydrodimerisation into an organic synthetic method: vapour pressure selectivity and the behaviour of functionalised substrates", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 111, no. 8, 12 April 1989 (1989-04-12), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 2935 - 2946, XP002274699, ISSN: 0002-7863
H. DHIMANE, ET AL.: "Réduction duplicative d'acétals dérivés d'aldhéhydes aromatiques par la combinaison bimétallique aluminium/plomb: préparation de 1,2-diaryl-1,2-diméthoxyéthanes", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, no. 2, March 1990 (1990-03-01), SOCIETE FRANCAISE DE CHIMIE, PARIS, FR, pages 283 - 291, XP002274700, ISSN: 0037-8968
F. GAGOSZ, ET AL.: "A direct approach to alpha-trifluoroamines", ORGANIC LETTERS, vol. 5, no. 15, 1 July 2003 (2003-07-01), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 2655 - 2657, XP002274506, ISSN: 1523-7060
P. DELDUC, ET AL.: "A convenient source of alkyl and acyl radicals", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 4, 15 February 1988 (1988-02-15), ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH., GB, pages 308 - 310, XP002274695, ISSN: 0022-4936
J. BOIVIN, ET AL.: "A flexible, convergent approach to piperidines, pyridines, azepines, and related derivatives", TETRAHEDRON LETTERS, vol. 40, no. 19, 7 May 1999 (1999-05-07), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 3701 - 3704, XP004163809, ISSN: 0040-4039
A. LIARD, ET AL.: "A new synthesis of alpha-tetralones", TETRAHEDRON LETTERS, vol. 38, no. 10, 10 March 1997 (1997-03-10), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 1759 - 1762, XP004054986, ISSN: 0040-4039
B. QUICLET-SIRE, ET AL.: "An unusual route to deoxysugars by hydrogen atom transfer from cyclohexane. Possible manifestation of polar effects in a radical process", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 118, no. 38, 25 September 1996 (1996-09-25), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 9190 - 9191, XP002244969, ISSN: 0002-7863
A. LIARD, ET AL.: "A practical method for the reductive cleavage of the sulfide bond in xanthates", TETRAHEDRON LETTERS, vol. 37, no. 33, 12 August 1996 (1996-08-12), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 5877 - 5880, XP004030563, ISSN: 0040-4039
T. NAKAI, ET AL.: "Potential synthetic utility of [3,3]-sigmatropic rearrangement of S-allyl dithiocarbamates. New routes to alpha,beta-unsaturated aldehydes", TETRAHEDRON LETTERS, no. 41, October 1974 (1974-10-01), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 3625 - 3628, XP002244970, ISSN: 0040-4039
DATABASE CHEMABS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002274701, retrieved from STN Database accession no. 2003:396832
T. HIRAO, ET AL.: "Catalytic pinacol coupling in the presence of acylating agent", SYNLETT, no. 11, November 2000 (2000-11-01), THIEME VERLAG, STUTTGART, DE, pages 1658 - 1660, XP002274696, ISSN: 0936-5214, Retrieved from the Internet
C.M. HU, ET AL.: "Synthesis of functionalised organic molecules containing a tetrafluoroethylene fragment by cobaloxime-promoted fluoroalkylation with substituted tetrafluoroethyl bromides", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 3, 7 February 1993 (1993-02-07), ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH, GB, pages 331 - 334, XP002274697
J. MÖNIG, ET AL.: "One-electron reduction of halothane (2-bromo-2-chloro-1,1,1-trifluoroethane) by free radicals. Radiation chemical model system for reductive metabolism", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS II, no. 12, 1984, ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH, GB, pages 2057 - 2063, XP002274698, ISSN: 0300-9580
S.H. BROWN, ET AL.: "Making mercury-photosensitised dehydrodimerisation into an organic synthetic method: vapour pressure selectivity and the behaviour of functionalised substrates", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 111, no. 8, 12 April 1989 (1989-04-12), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 2935 - 2946, XP002274699, ISSN: 0002-7863
H. DHIMANE, ET AL.: "Réduction duplicative d'acétals dérivés d'aldhéhydes aromatiques par la combinaison bimétallique aluminium/plomb: préparation de 1,2-diaryl-1,2-diméthoxyéthanes", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, no. 2, March 1990 (1990-03-01), SOCIETE FRANCAISE DE CHIMIE, PARIS, FR, pages 283 - 291, XP002274700, ISSN: 0037-8968
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