메뉴 건너뛰기




Volumn , Issue 12, 1997, Pages 1433-1438

1,4-Diazabicyclo[2.2.2]octane (DABCO)- an efficient reagent in the synthesis of alkyl tosylates or sulfenates

Author keywords

1,4 Diazabicyclo 2,2,2 octane; DABCO; Sterically hindered alcohols; Sulfenic acid O ester; Tosylation

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; ALKYL SULFENATE; ALKYL TOSYLATE; CHLOROFORM; DICHLOROMETHANE; SOLVENT; SULFENIC ACID DERIVATIVE; TERTIARY AMINE; UNCLASSIFIED DRUG;

EID: 0031434270     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1372     Document Type: Article
Times cited : (52)

References (57)
  • 1
    • 0000969553 scopus 로고
    • Alkyl Chalcogenides: Sulfur-based Functional Groups
    • Katritzky, A.R.; Meth-Cohn, O.; Rees, C.W., Eds.; Pergamon: Cambridge
    • Bulman Page, P.C.; Wilkes, R.D.; Reynolds, D. Alkyl Chalcogenides: Sulfur-based Functional Groups. In Comprehensive Organic Functional Group Transformations; Katritzky, A.R.; Meth-Cohn, O.; Rees, C.W., Eds.; Pergamon: Cambridge, 1995; Vol. 2, pp 194-202.
    • (1995) Comprehensive Organic Functional Group Transformations , vol.2 , pp. 194-202
    • Bulman Page, P.C.1    Wilkes, R.D.2    Reynolds, D.3
  • 2
    • 0010659422 scopus 로고
    • Vinyl and Aryl Chalcogenides: Sulfur-, Selenium-and Tellurium-based Functional Groups
    • Katritzky, A.R.; Meth-Cohn, O.; Rees, C.W., Eds.; Pergamon: Cambridge
    • Taylor, P.C. Vinyl and Aryl Chalcogenides: Sulfur-, Selenium-and Tellurium-based Functional Groups. In Comprehensive Organic Functional Group Transformations, Katritzky, A.R.; Meth-Cohn, O.; Rees, C.W., Eds.; Pergamon: Cambridge, 1995; Vol. 2, p 720.
    • (1995) Comprehensive Organic Functional Group Transformations , vol.2 , pp. 720
    • Taylor, P.C.1
  • 3
    • 0001153987 scopus 로고
    • Carboxylic Esters and Lactones
    • Katritzky, A.R.; Meth-Cohn, O.; Rees, C.W., Eds.; Pergamon: Cambridge
    • Mulzer, J. Carboxylic Esters and Lactones. In Comprehensive Organic Functional Group Transformations; Katritzky, A.R.; Meth-Cohn, O.; Rees, C.W., Eds.; Pergamon: Cambridge, 1995; Vol. 5, pp 121-179.
    • (1995) Comprehensive Organic Functional Group Transformations , vol.5 , pp. 121-179
    • Mulzer, J.1
  • 4
    • 0010705791 scopus 로고
    • Herstellung von Sulfensäureestern
    • Müller, E., Ed.; Schwefel-, Selen-, Tellurverbindungen, 4th ed., Thieme: Stuttgart
    • Schöberl, A.; Wagner, A. Herstellung von Sulfensäureestern. In Houben-Weyl, Methoden der Organischen Chemie; Müller, E., Ed.; Vol 9, Schwefel-, Selen-, Tellurverbindungen, 4th ed., Thieme: Stuttgart, 1955; pp 267-283.
    • (1955) Houben-Weyl, Methoden der Organischen Chemie , vol.9 , pp. 267-283
    • Schöberl, A.1    Wagner, A.2
  • 5
    • 0010700341 scopus 로고
    • Sulfensäureorganoester aus Sulfensäurehalogeniden
    • Klamann, D., Ed.; Organische Schwefel-Verbindungen I, 4th ed.; Thieme: Stuttgart
    • Schubart, R. Sulfensäureorganoester aus Sulfensäurehalogeniden. In Houben-Weyl, Methoden der Organischen Chemie; Klamann, D., Ed.; Vol E11, Organische Schwefel-Verbindungen I, 4th ed.; Thieme: Stuttgart, 1985; pp 101-104.
    • (1985) Houben-Weyl, Methoden der Organischen Chemie , vol.E11 , pp. 101-104
    • Schubart, R.1
  • 6
    • 0010740372 scopus 로고
    • Sulfonsäure-ester aus Sulfonylhalogeniden
    • Müller, E., Ed.; Schwefel-, Selen-, Tellur-Verbindungen, 4th ed.; Thieme: Stuttgart
    • Muth, F. Sulfonsäure-ester aus Sulfonylhalogeniden. In Houben-Weyl, Methoden der Organischen Chemie; Müller, E., Ed.; Vol 9, Schwefel-, Selen-, Tellur-Verbindungen, 4th ed.; Thieme: Stuttgart, 1955; pp 665-670.
    • (1955) Houben-Weyl, Methoden der Organischen Chemie , vol.9 , pp. 665-670
    • Muth, F.1
  • 7
    • 0010701215 scopus 로고
    • Arylsulfonsäuren
    • Klamann, D., Ed.; Organische Schwefel-Verbindungen II, 4th ed.; Thieme: Stuttgart
    • Pawlenko, S. Arylsulfonsäuren. In Houben-Weyl, Methoden der Organischen Chemie; Klamann, D., Ed.; Vol E11, Organische Schwefel-Verbindungen II, 4th ed.; Thieme: Stuttgart, 1985; pp 1090-1092.
    • (1985) Houben-Weyl, Methoden der Organischen Chemie , vol.E11 , pp. 1090-1092
    • Pawlenko, S.1
  • 8
    • 0010743503 scopus 로고
    • Offenkettige Carbonsäureester aus Carbonsäurechloriden und Alkoholen
    • Falbe, J., Ed.; Carbonsäuren und Carbonsäure-Derivate I, 4th ed.; Thieme: Stuttgart
    • Pielartzik, H.; Irmisch-Pielartzik, B.; Eicher, T. Offenkettige Carbonsäureester aus Carbonsäurechloriden und Alkoholen. In Houben-Weyl, Methoden der Organischen Chemie; Falbe, J., Ed.; Vol E5, Carbonsäuren und Carbonsäure-Derivate I, 4th ed.; Thieme: Stuttgart, 1985; pp 695-698.
    • (1985) Houben-Weyl, Methoden der Organischen Chemie , vol.E5 , pp. 695-698
    • Pielartzik, H.1    Irmisch-Pielartzik, B.2    Eicher, T.3
  • 15
    • 0141546825 scopus 로고
    • Preparation of Sulfonic Acids, Esters, Amides and Halides
    • Patai, S.; Rappoport, Z., Eds.; Wiley: New York
    • Hoyle, J. Preparation of Sulfonic Acids, Esters, Amides and Halides. In The Chemistry of Sulfonic Acids, Esters and their Derivatives; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1991; pp 366-379.
    • (1991) The Chemistry of Sulfonic Acids, Esters and Their Derivatives , pp. 366-379
    • Hoyle, J.1
  • 16
    • 0000986779 scopus 로고
    • Reactivity of Pyridines and Their Benzo Derivatives: Reactivity at Ring Atoms
    • Katritzky, A.R.; Rees, C.W., Eds.; Pergamon: Oxford
    • Scriven, E.F.V. Reactivity of Pyridines and Their Benzo Derivatives: Reactivity at Ring Atoms. In Comprehensive Heterocyclic Chemistry, Katritzky, A.R.; Rees, C.W., Eds.; Pergamon: Oxford, 1994; Vol. 2, pp 166-313.
    • (1994) Comprehensive Heterocyclic Chemistry , vol.2 , pp. 166-313
    • Scriven, E.F.V.1
  • 18
    • 34548002324 scopus 로고    scopus 로고
    • unpublished results for
    • Hünig, S.; Wenner, H. unpublished results for:
    • Hünig, S.1    Wenner, H.2
  • 24
    • 34547999814 scopus 로고    scopus 로고
    • 9b
    • 9b
  • 27
    • 84944593405 scopus 로고
    • Chem. Abstr. 1986, 105, 225961a.
    • (1986) Chem. Abstr. , vol.105
  • 29
  • 34
    • 34548001908 scopus 로고    scopus 로고
    • note
    • 3N afforded after a reaction period of 24 h (-)-menthyl tosylate 3d in 53% yield.
  • 35
    • 34548000652 scopus 로고    scopus 로고
    • note
    • Treatment of a solution of DABCO (2 equivalents) with TosCl (1.5 equivalents) afforded a colorless precipitate which was stirred for 18 h at ambient temperatures. Hereafter 1 equivalent of (-)-menthol 2d was added and the slurry was allowed to stir for 14 h at r.t.. Workup of the reaction mixture afforded 72% of (-)-menthyl tosylate 3d.
  • 36
    • 34548001331 scopus 로고    scopus 로고
    • note
    • The mixtures remained, however, thick slurries throughout the reaction periods because of the formation of hardly soluble DABCO·HCl during the course of the conversion of the alcohols 2.
  • 37
    • 34548000799 scopus 로고    scopus 로고
    • note
    • 3) δ = 21.5, 40.7, 45.9, 52.2, 59.2, 127.9, 129.7, 132.5, 143.7. MS (EI, 70 eV): m/z (%) = 302 (M + , 7), 253 (40), 147 (100).
  • 38
    • 34548000425 scopus 로고    scopus 로고
    • The use of ultrasound (Table 2, entry 9) may help to increase the yield of tosylates 3 from the heterogeneous mixtures
    • The use of ultrasound (Table 2, entry 9) may help to increase the yield of tosylates 3 from the heterogeneous mixtures.
  • 43
    • 34548000191 scopus 로고
    • Synthesis of Sulfenic Acids and Esters
    • Patai, S.; Rappoport, Z., Eds.; Wiley: New York
    • For further methods for the preparation of sulfenates see: Drabowicz, J.; Lyzwa, P.; Mikolajczyk, M. Synthesis of Sulfenic Acids and Esters. In The Chemistry of Sulfenic Acids and their Derivatives; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1990; pp 205-218.
    • (1990) The Chemistry of Sulfenic Acids and Their Derivatives , pp. 205-218
    • Drabowicz, J.1    Lyzwa, P.2    Mikolajczyk, M.3
  • 44
    • 34548001962 scopus 로고    scopus 로고
    • note
    • 3N which is commonly used in the synthesis of 2,4-dinitrobenzenesulfenates 4.
  • 45
    • 34548000023 scopus 로고    scopus 로고
    • note
    • 3)]}.
  • 47
    • 0000901649 scopus 로고
    • Optically active sulfonamides, e.g. ethyl (S)-N-(p-toluenesulfonyl)phenylalanate (73 %), ethyl (S)-N-[(S)-camphorsulfonyl]phenylalanate (90 %), (R)-1-phenyl-N-(p-toluenesulfonyl)-ethanamide (91 %), trans-(R,R)-N,N′-bis(p-toluenesulfonyl) 1,2-cyclohexanediamide (80 %), have been prepared using DABCO as base: Gerlach, U.; Haubenreich, T.; Hünig, S. Chem. Ber. 1994, 127, 1969.
    • (1994) Chem. Ber. , vol.127 , pp. 1969
    • Gerlach, U.1    Haubenreich, T.2    Hünig, S.3
  • 56
    • 34548001453 scopus 로고    scopus 로고
    • Tosylation studies using primary alcohols (not shown in Table 1) indicate that these substrates are converted to the respective tosylates within 1-3 h. It is advantageous to work up these mixtures immediately rather than allowing an extension of the reaction period to 24 h
    • Tosylation studies using primary alcohols (not shown in Table 1) indicate that these substrates are converted to the respective tosylates within 1-3 h. It is advantageous to work up these mixtures immediately rather than allowing an extension of the reaction period to 24 h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.