24
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

The Chemistry of Chlorodithioformates

, , &
Pages 235-291 | Received 30 Jun 1994, Published online: 04 Oct 2006

References

  • Permanent address: Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Kom, Egypt.
  • Permanent address: Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt.
  • Department of Chemistry and Chemical Engineering, The Engineering Academy of Denmark, Building 376, DK-2800 Lyngby, Denmark.
  • Fabian , J. , Viola , H. and Mayer , R. 1967 . Tetrahedron , 23 : 4323
  • Kraatz , U. 1983 . Houben-Weyl , E4 : 414
  • Nilsson , N. H. 1974 . J. Chem. Soc., Perkin Trans. , 1 : 1308
  • Arndt , F. , Milde , E. and Eckert , G. 1923 . Ber. , 56 : 1976
  • Klason , P. 1887 . Ber. , 20 : 2376
  • Braun , J. V. 1902 . Ber. , 35 : 3377
  • Rivier , H. and Richard , P. 1925 . Helv. Chim. Acta , 8 : 499
  • Jensen , K. A. 1937 . J. Prakt. Chem. , 148 : 101
  • Godet , H. C. and Wann , R. E. 1961 . J. Org. Chem. , 26 : 4047
  • Goerdeler , J. and Hohage , H. 1973 . Chem. Ber. , 106 : 1487
  • McKinnon , D. M. and Queen , A. 1972 . Can. J. Chem. , 50 : 1401
  • Bögemann , M. , Petersen , S. , Schultz , O. E. and Söll , H. 1955 . Houben-Weyl , 9 : 808
  • Sturm , B. and Gattow , G. 1984 . Z. Anorg. Allg. Chem. , 508 : 136
  • Houben , J. and Schultze , K. M. L. 1911 . Ber. , 44 : 3226
  • Blackman , L. C. F. and Dewar , M. J. S. 1957 . J. Chem. Soc. , : 162
  • Engelhard , E. L. , Iumma , W. C. Jr. and Saari , W. Ger. Offen. . 2,433,397 . 1975 . Chem. Abstr. 82, 156377g (1981).
  • Demaree , P. , Doria , M. and Muchowski , J. 1978 . J. Heterocycl. Chem. , 15 : 1295
  • Ishii , F. , Uchida , T. , Miura , A. and Tsuruta , M. Jpn. Kokai Tokkyo Koho . 01,206,338 [89,206,338] . 1989 . Chem. Abstr. 112, 45610w (1990). Konica Co.
  • Goerdeler , J. , Hohage , H. and Zeid , I. 1976 . Chem. Ber. , 109 : 3108
  • Birum , G. H. U. S. Pat. . 3,116,335 . 1963 . Chem. Abstr. 60, 10549d (1964).
  • El-Sayed , I. , Abdel-Megeed , M. F. , Yassin , S. M. and Senning , A. unpublished results.
  • Viola , H. and Mayer , R. Ger. (East) . 82,464 . 1971 . Chem. Abstr. 77, 4957e (1972).
  • River , M. H. 1907 . Bull. Soc. Chim. Fr. [4] , 1 : 733
  • Duus , F. 1979 . Compr. Org. Chem. , 3 : 434
  • Hart , R. M. and Whitehead , M. A. 1971 . Can. J. Chem. , 49 : 2508
  • Hass , A. and Kampf , K. W. 1984 . Tetrahedron , 40 : 4963
  • Hanse , H. C. , Jensen , B. and Senning , A. 1985 . Sulfur Lett. , 3 : 61
  • Hansen , H. C. , Senning , A. and Hazell , R. G. 1985 . Tetrahedron , 41 : 5145
  • Kaji , A. 1961 . Bull. Chem. Soc. Jpn. , 34 : 1147
  • Lindgren , B. , Lindgren , G. , Artursson , E. , Puu , G. , Fredriksson , J. and Andersson , M. 1985 . J. Enzym. Inhib. , 1 : 1
  • Nakayama , J. , Dan , S. and Hoshino , M. 1981 . J. Chem. Soc., Perkin Trans. , 1 : 413
  • Tangerman , A. and Zwanenburg , B. 1975 . J. Chem. Soc., Perkin Trans. , 2 : 916
  • Anthoni , U. , Dahl , B. M. , Eggert , H. , Larsen , C. and Nielsen , P. H. 1979 . Acta Chem. Scand. , B30 : 71
  • Charlton , J. L. , Loosmore , M. S. and McKinnon , D. M. 1974 . Can. J. Chem. , 52 : 3021
  • Benati , L. and Montevecchi , P. C. 1976 . J. Org. Chem. , 41 : 2640
  • Digenis , G. A. , Agha , B. J. and Tsuji , K. U. S. US . 4,643,991 . 1987 . Chem. Abstr. 106, 214398s (1987).
  • Viola , H. and Mayer , R. 1979 . Z. Chem. , 19 : 289
  • Mizhiritskii , M. D. and Reikshfeld , V. O. 1986 . Zh. Obshch. Khim. , 56 : 1547 J. Gen. Chem. 56, 1373 (1987).
  • Haas , A. 1971 . Gmelins Handbook of Inorganic Chemistry, Perfluorohalogen Compounds , 9 : 28 and references cited therein.
  • Hansen , H. C. 1980 . Cand. Scient. Thesis Aarhus University .
  • Ried , W. and Beck , B. M. 1964 . Justus Liebigs Ann. Chem. , 673 : 124
  • Sharma , S. 1986 . Sulfur Rep. , 5 : 1
  • Bunnenberg , R. and Jochims , J. C. 1981 . Chem. Ber. , 114 : 1132
  • Senning , A. 1981 . IUPAC Organic Sulfur Chemistry , Edited by: Freidlina , R. Kh. and Skorova , A. E. 151 Oxford New York : Pergamon Press .
  • Kühle , E. 1973 . Angew. Chem. Int. Ed. Engl. , 12 : 630
  • Moltzen , E. K. , Klabunde , K. J. and Senning , A. 1988 . Chem. Rev. , 88 : 391
  • Moltzen , E. K. 1985 . Cand. Scient. Thesis Aarhus University .
  • Klabunde , K. J. , Kramer , M. P. , Senning , A. and Moltzen , E. K. 1984 . J. Am. Chem. Soc. , 106 : 263
  • Moltzen , E. K. , Senning , A. , Kramer , M. P. and Klabunde , K. J. 1984 . J. Org. Chem. , 49 : 3854
  • Moltzen , E. K. and Senning , A. 1986 . Sulfur Lett. , 4 : 97
  • Moltzen , E. K. , Jensen , B. and Senning , A. 1986 . Sulfur Lett. , 4 : 203
  • Kramer , M. P. 1985 . Ph. D. Thesis Kansas State University .
  • Moltzen , E. K. , Kramer , M. P. , Senning , A. and Klabunde , K. J. 1987 . J. Org. Chem. , 52 : 1156
  • Klabunde , K. J. , Moltzen , E. K. and Voska , K. 1989 . Phosphorus, Sulfur, Silicon , 43 : 47
  • Nielsen , J. and Senning , A. 1991 . Sulfur Lett. , 12 : 143
  • Nielsen , J. 1990 . Cand. Scient. Thesis Aarhus University .
  • Moltzen , E. K. , Jensen , B. and Senning , A. 1986 . Act. Chem. Scand. , B40 : 609
  • Brois , S. J. and Gutierrez , A. U. S. . 4,239,636 . 1980 . Chem. Abstr. 94, 194802 (1981). (Exxon Research and Engineering Co.)
  • Berenbaum , M. B. and Gobran , R. H. U. S. . 3,128,271 . 1964 . Chem. Abstr. 61, 2038 (1964).(Thiokol Chemical Corp.)
  • [822-38-8]; Aldrich Catalog no. E2,775-0.
  • Sturm , B. and Gattow , G. 1983 . Z. Anorg. Allg. Chem. , 502 : 7
  • Dunn , A. D. and Rudorf , W. D. 1989 . Carbon Disulfide in Organic Chemistry , 341 Chichester : Ellis-Horwood Ltd .
  • Benati , L. and Montevecchi , P. C. 1977 . J. Org. Chem. , 42 : 2025 eidem, ibid. 41, 2639 (1976).
  • Mott , A. W. and Barany , G. 1984 . Sulfur Lett. , 2 : 241
  • Barany , G. 1983 . Tetrahedron Lett. , 24 : 5683
  • Barany , G. , Schroll , A. L. , Mott , A. W. and Halsrud , D. A. 1983 . J. Org. Chem. , 48 : 4750
  • Commeyrase , A. , Blancou , H. and Moreau , P. Ger. Offen . 2,708,751 . 1977 . Chem. Abstr. 87, 183970e (1977).
  • Blancou , H. and Commeyras , A. 1982 . J. Fluorine Chem. , 20 : 267
  • Haas , A. and Yazdanbakshch , M. 1976 . Chem. Ber. , 109 : 1976
  • Senning , A. 1979 . Angew. Chem. , 91 : 1006
  • Senning , A. , Hansen , H. C. , Abdel-Megeed , M. F. , Mazurkiewicz , W. and Jensen , B. 1986 . Tetrahedron , 42 : 739
  • Ishii , A. , Akazawa , T. , Ding , M.-X. , Honjo , T. , Nakayama , J. and Hoshino , M. 1993 . J. Am. Chem. Soc. , 115 : 4914
  • Schaumann , E. 1988 . Tetrahedron , 44 : 1827
  • Fabian , J. 1972 . Z. Phys. Chem. (Leipzig) , 250 : 377
  • Bock , H. , Wittel , K. and Haas , A. 1974 . Z. Anorg. Allg. Chem. , 408 : 107
  • Solouki , B. , Rosmus , P. and Bock , H. 1976 . J. Am. Chem. Soc. , 98 : 6054
  • Bock , H. , Hirabayashi , T. and Mohmand , S. 1982 . Chem. Ber. , 115 : 492
  • Ohno , A. , Nakamura , K. , Nakazima , Y. and Oka , S. 1975 . Bull. Chem. Soc. Jpn. , 48 : 2403
  • Scheithauer , S. and Mayer , R. 1979 . “ Thio- and Dithiocarboxylic Acids and Their Derivatives ” . In Topics in Sulfur Chemistry , Edited by: Senning , A. Vol. 4 , 192ff Stuttgart : Georg Thieme Verlag . and references cited therein.
  • Gombler , W. 1981 . Z. Naturforsch., B: Anorg. Chem. , 36B : 1561
  • Hart , R. M. and Whitehead , M. A. 1971 . Can. J. Chem. , 49 : 2508
  • Andrieu , C. G. , Metzner , P. , Debruyne , D. , Bertin , D. M. and Lumbroso , H. 1977 . J. Mol. Struct. , 39 : 263
  • Viola , H. , Scheithauer , S. and Mayer , R. 1968 . Chem. Ber. , 101 : 3517
  • Voss , J. 1979 . The Chemistry of Acid Derivativs , Edited by: Patai , S. 1021 Chichester : John Wiley & Sons . Suppl. B, Part 2
  • Mayer , R. and Scheithauer , S. 1985 . Houben-Weyl , E5 : 891
  • Ramadas , S. R. , Srinivasan , P. S. , Ramachandran , J. and Sastry , V. V. S. K. 1983 . Synthesis , : 605
  • Haraoubia , R. , Gressier , J.-C. and Levesque , G. 1982 . Makromol. Chem. , 183 : 2367
  • Haas , A. and Wanzk , W. 1987 . Chem. Ber. , 120 : 429
  • Bruckner , C. and Reissig , H.-U. 1988 . Justus Liebigs Ann. Chem. , : 465
  • Hartke , K. and Hoederath , W. 1983 . Sulfur Lett. , 1 : 191
  • Hartke , K. and Peshkar , L. 1968 . Arch. Pharm. (Weinheim) , 301 : 601 eidem, Pharm. Zentralhalle 107, 348 (1968); K. Hartke and L. Seib, Pharmazie 25, 517 (1970); K. Hartke and F. Meissner, Tetrahedron 28, 875 (1972).
  • Larsson , F. C. V. and Lawesson , S.-O. 1975 . Recl. Trav. Chim. Pays-Bas , 94 : 1
  • Aufauvre , Y. , Verny , M. and Vessiere , R. 1973 . Bull. Soc. Chim. Fr. , : 1373
  • Viola , H. 1969 . Dissertation Dresden : Technical University .
  • Viola , H. and Mayer , R. 1976 . Z. Chem. , 16 : 355
  • Nilsson , N. H. , Senning , A. , Karlsson , S. and Sandström , J. 1972 . Synthesis , : 314
  • Nilsson , N. H. 1974 . Tetrahedron , 30 : 3181
  • Christiane , B. and Reibig , H. U. 1988 . Justus Liebigs Ann. Chem. , : 465
  • Hartke , K. , Kunze , O. and Hoederath , W. 1985 . Synthesis , : 960
  • Hartke , K. , Gerber , H.-D. and Roesrath , U. 1989 . Tetrahedron Lett. , 30 : 1073
  • Hartke , K. , Gerber , H.-D. and Roesrath , U. 1991 . Justus Liebigs Ann. Chem. , : 903
  • Crosby , D. G. and Niemann , C. 1954 . J. Amer. Chem. Soc. , 76 : 4458
  • Rieche , A. , Hilgetag , G. , Martin , D. and Kreyzi , I. 1963 . Arch. Pharm. (Weinheim) , 296 : 310
  • Walter , W. and Bode , K.-D. 1967 . Angew. Chem. , 79 : 285
  • Lotz , S. and Gattow , G. 1990 . Z. Anorg. Allg. Chem. , 581 : 99
  • Lotz , S. and Gattow , G. 1990 . Z. Anorg. Allg. Chem. , 585 : 151
  • Lotz , S. and Gattow , G. 1990 . Z. Anorg. Allg. Chem. , 585 : 142
  • Digenis , G. A. , Agha , J. B. and Tsuji , K. U. S. US . 4,643,991 . 1984 . Chem. Abstr. 106, 214398s (1987).
  • Carlsen , L. and Egsgaard , H. 1987 . Chem. Ber. , 120 : 987
  • Takematsu , T. , Konnai , M. , Nishida , T. , Hosogai , T. , Mizano , M. and Shiguro , M. I. Jpn. Kokai Tokkyo Koho . 79,145,654 . 1979 . Chem. Abstr. 92, 198267h (1980).
  • Tomalia , D. A. , Sheetz , D. P. and Ham , G. E. 1970 . J. Org. Chem. , 35 : 47
  • Fishbein , P. L. and Kohn , H. 1987 . J. Med. Chem. , 30 : 1967
  • Takematsu , T. , Konnai , M. , Nishida , T. , Hosogai , T. , Mizuno , M. and Ishiguro , M. Jpn. Kokai Tokkyo Koho . 79,145,215 . 1979 . Chem. Abstr. 92, 141806d (1980).
  • Takematsu , T. , Konnai , M. , Nishida , T. , Hosogai , T. , Mizano , M. and Ishiguro , M. Jpn. Kokai Tokkyo Koho . 79,145,214 . 1979 . Chem. Abstr. 92, 141805c (1980).
  • Fischer , A. , Hansen , H. and Rucher , W. Ger. Offen . 2,312,045 . 1974 . Chem. Abstr. 82, 4108g (1975).
  • Voigt , C. W. and Gattow , G. 1978 . Z. Anorg. Allg. Chem. , 438 : 195
  • Barton , D. H. R. , Crich , D. and Potier , P. 1985 . Tetrahedron Lett. , 26 : 5943
  • Skorini , S. J. 1979 . Cand. Scient. Thesis 32 Aarhus University .
  • Skorini , S. J. and Senning , A. 1980 . Tetrahedron , 36 : 539
  • Gattow , G. and Lotz , S. 1986 . Z. Anorg. Allg. Chem. , 533 : 99
  • Schubert , G. and Gattow , G. 1989 . Z. Anorg. Allg. Chem. , 579 : 129
  • Lieber , E. , Pillai , C. N. , Ramachandran , J. and Hites , R. D. 1957 . J. Org. Chem. , 22 : 1750
  • Lieber , E. , Oftendahl , I. and Rao , C. N. R. 1963 . J. Org. Chem. , 28 : 194
  • McKinnon , D. M. and Queen , A. 1972 . Can. J. Chem. , 50 : 1401
  • Queen , A. and Matts , T. C. 1975 . Tetrahedron Lett. , : 1503
  • Kricheldorf , H.-R. 1974 . Synthesis , : 561
  • Hantzsch , A. and Hirsch , B. 1896 . Ber. , 29 : 947
  • Beckwith , A.-L. J. , Bowry , V. W. and Schiesser , C. H. 1991 . Tetrahedron , 47 : 121
  • Sakanone , S. , Hawusawa , S. , Yamazaki , N. , Yoneda , R. and Kurihara , T. 1990 . Chem. Pharm. Bull. , 38 : 2981
  • Barton , D. H. R. , Jang , D. O. and Jaszberenyi , J. Cs. 1991 . Synlett. , : 435
  • Lüders , W. , Salbeck , G. , Bauer , J. and Bieringer , H. Ger. Offen. DE . 3,818,848 . 1989 . Chem. Abstr. 112, 235333f (1990).
  • Traber , W. and Weiss , A. Swiss . 544,745 . 1974 . Chem. Abstr. 80, 82424e (1974).
  • Lieber , E. , Rao , C. N. , Chao , T. S. and Hoffman , C. W. W. 1957 . Anal. Chem. , 2 : 916
  • Sneen , R. A. and Robbins , H. W. 1969 . J. Am. Chem. Soc. , 91 : 3100
  • Sneen , R. A. and Larsen , A. W. 1969 . J. Am. Chem. Soc. , 91 : 6031
  • Kohnstam , G. 1967 . Adv. Phys. Org. Chem. , 5 : 121
  • Queen , A. 1967 . Can. J. Chem. , 45 : 1619
  • Queen , A. , McKinnon , D.-M. and Bell , A. W. 1976 . Can. J. Chem. , 54
  • Masson , S. and Sene , A. 1988 . Phosphorus Sulfur , 40 : 1
  • Birum , G. H. U. S. . 3,089,891 . 1963 . Chem. Abstr. 63, 5678h (1966).
  • Bashour , J. T. U. S. . 2,676,129 . 1954 . Chem. Abstr. 48, 8472i (1954).
  • Bashour , J. T. U. S. . 2,731,487 . 1956 . Chem. Abstr. 50, 15583h (1956).
  • Renner , H. J. , Schneider , G. and Weissflog , J. Ger. (East) . 15,431 . 1958 . Chem. Abstr. 54, 2650f (1960).
  • Blake , E. S. U. S. Patent . 2,396,487 . 1946 . Chem. Abstr. 40, 2974 (1946).
  • Brokke , M. E. and Stoffey , D. G. U. S. . 3,247,052 . 1966 . Chem. Abstr. 69, 1598t (1968).
  • Takamizawa , A. and Hirai , K. Jpn. . 72,43,951 . 1972 . Chem. Abstr. 78, 97702b (1973).
  • Sturm , B. and Gattow , G. 1984 . Z. Anorg. Allg. Chem. , 512 : 231
  • Nilsson , N. H. and Senning , A. 1974 . Chem. Ber. , 107 : 2345
  • Nilsson , N. H. , Jacobsen , C. and Senning , A. 1971 . Chem. Commun. , : 314
  • Drabowicz , J. , Kielbasinski , P. and Mikolajzyk , M. 1990 . The Chemistry of Sulfenic Acids, Esters and Their Derivatives , Edited by: Patai , S. 376 Chichester : John Wiley and Sons Ltd. .
  • Hansen , H. C. and Senning , A. 1980 . J. Chem. Soc., Chem. Commun. , : 692
  • Hansen , H. C. and Senning , A. 1979 . J. Chem. Soc., Chem. Commun. , : 1135
  • Senning , A. , Hansen , H. C. and Skorini , S. J. 1979 . Phosphorus Sulfur , 5 : 359
  • Holm , S. , Boerma , J. A. , Nilsson , N. H. and Senning , A. 1976 . Chem. Ber. , 109 : 1069
  • Boerma , J. A. , Nilsson , N. H. and Senning , A. 1974 . Tetrahedron , 30 : 2735
  • Holm , S. and Senning , A. 1973 . Tetrahedron Lett. , : 2389
  • Nilsson , N. H. and Senning , A. 1975 . Organic Sulfur Chemistry , Edited by: Stirling , C. J. M. 414 London : Butterworths .
  • Nilsson , N. H. , Jacobsen , C. and Senning , A. 1970 . Chem. Commun. , : 658
  • Twiss , D. 1927 . J. Am. Chem. Soc. , 49 : 490
  • Sturm , B. and Gattow , G. 1984 . Z. Anorg. Allg. Chem. , 514 : 129
  • Didderich , G. and Haas , A. 1976 . Chem. Ber. , 109 : 3432
  • Zwanenburg , B. and Strating , J. 1970 . Quart. Rep. Sulfur Chem. , 5 : 89
  • Hansen , H. C. and Senning , A. 1985 . Org. Prep. Proced. Int. , 17 : 275
  • Böhme , H. , Brinkmann , M. and Steudel , H.-P. 1981 . Justus Liebigs Ann. Chem. , : 244
  • Barany , G. and Mott , A. W. 1984 . J. Org. Chem. , 49 : 1043
  • Still , I. W. J. , Kutney , G. and McLean , D. 1982 . J. Org. Chem. , 47 : 555
  • Haas , A. and Kampf , K. W. 1984 . Tetrahedron , 40 : 4963
  • Didderich , G. , Haas , A. and Yazdanbakhsch , M. 1977 . Chem. Ber. , 110 : 616
  • Demaree , P. , Doria , M. C. and Muchowski , J. M. 1977 . Can. J. Chem. , 55 : 243
  • Beiner , J. M. , Lecadet , D. , Paquer , D. , Thuillier , A. and Vialle , J. 1973 . Bull. Soc. Chim. Fr. , : 1979
  • Millard , B. J. and Pain , D. L. 1970 . J. Chem. Soc. C , : 2042
  • Zeller , K. P. , Meier , H. and Müller , E. 1972 . Tetrahedron , 28 : 1353
  • Baker , B. R. , Quarry , M. V. , Bernstein , S. , Safir , S. R. and Subarow , Y. 1947 . J. Org. Chem. , 12 : 167
  • Goerdeler , J. , Ohm , J. and Tegtmeyer , O. 1956 . Chem. Ber. , 89 : 1534
  • Demaree , P. , Doria , M. and Muchowski , J. M. 1978 . J. Heterocycl. Chem. , 15 : 1295
  • Horning , D. E. and Muchowski , J. M. 1973 . Can. J. Chem. , 51 : 2349
  • Lacasse , G. and Muchowski , J. M. 1973 . ibid. , 51 : 2353
  • Marshall , J. A. and Partridge , J. J. 1968 . J. Org. Chem. , 33 : 4090
  • Audrieth , L. F. , Johnson , J. R. , Brown , A. W. and Mason , C. W. 1930 . J. Am. Chem. Soc. , 52 : 1928
  • Sturm , B. and Gattow , G. 1984 . Z. Anorg. Allg. Chem. , 509 : 67
  • Dean , W. K. 1977 . J. Organometal. Chem. , 135 : 195
  • Nilsson , N. H. and Senning , A. 1980 . Org. Prep. Proced. Int. , 12 : 229
  • Inagaki , Y. and Okazaki , R. 1978 . Yuki Gosei Kagaku Kyokai Shi , 36 : 1 Chem. Abstr. 89, 41580v (1978).
  • Gattow , G. 1993 . Sulfur Rep. , 14 : 1
  • Senning , A. 1991 . Sulfur Lett. , 12 : 235
  • El-Sayed , I. , Abdel-Megeed , M. F. , Yassin , S. M. and Senning , A. 1992 . Sulfur Lett. , 15 : 1
  • El-Sayed , I. , Abdel-Megeed , M. F. , Yassin , S. M. and Senning , A. 1994 . Phosphorus, Sulfur, Silicon Relat. Elem. , 86 : 239

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.