메뉴 건너뛰기
Synlett
Volumn , Issue 14, 2007, Pages 2209-2212
o-benzenedisulfonimide: A novel and reusable catalyst for acid-catalyzed organic reactions
Author keywords

Acid catalyzed organic reactions; Br nsted acid; Dehydrative reactions; o Benzenedisulfonimide; Reusable catalyst
Indexed keywords

2 BENZENEDISULFONIMIDE; BENZENE DERIVATIVE; BRONSTED ACID; UNCLASSIFIED DRUG;
EID: 34548732384     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985559     Document Type: Article
Times cited : (26)
References (54)
  • 18
    • 0033607588 scopus 로고    scopus 로고
    • For recent works on acid-catalyzed dehydrative etherification, esterification, and acetalization reactions with metal catalysts, see for example: a
    • For recent works on acid-catalyzed dehydrative etherification, esterification, and acetalization reactions with metal catalysts, see for example: (a) Sharma, G. V. M.; Mahalingam, A. K. J. Org. Chem. 1999, 64, 8943.
    • (1999) J. Org. Chem , vol.64 , pp. 8943
    • Sharma, G.V.M.1    Mahalingam, A.K.2
  • 22
    • 84986535914 scopus 로고    scopus 로고
    • With solid-acid catalysis: (e) Scott, L. T.; Naples, J. O. Synthesis 1973, 209.
    • With solid-acid catalysis: (e) Scott, L. T.; Naples, J. O. Synthesis 1973, 209.
  • 27
    • 0033601097 scopus 로고    scopus 로고
    • In supercritical fluids: (j) Gray, W. K.; Smail, F. R.; Hitzler, M. G.; Ross, S. K.; Poliakoff, M. J. Am. Chem. Soc. 1999, 121, 10711.
    • In supercritical fluids: (j) Gray, W. K.; Smail, F. R.; Hitzler, M. G.; Ross, S. K.; Poliakoff, M. J. Am. Chem. Soc. 1999, 121, 10711.
  • 28
    • 0037140770 scopus 로고    scopus 로고
    • In ionic liquids: (k) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. Jr. J. Am. Chem. Soc. 2002, 124, 5962.
    • In ionic liquids: (k) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. Jr. J. Am. Chem. Soc. 2002, 124, 5962.
  • 29
    • 34548775712 scopus 로고    scopus 로고
    • WO 03086605, 325782
    • (l) Davis, J. H. Jr. WO 03086605, 2003; Chem. Abstr. 2003, 139, 325782.
    • (2003) Chem. Abstr , vol.139
    • Davis Jr., J.H.1
  • 32
  • 38
    • 34548775099 scopus 로고    scopus 로고
    • Bergstrom, R. G. In The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analogues, Suppl. E, Part 2; Wiley: Chichester, 1980, Chap. 20, 881-902.
    • (c) Bergstrom, R. G. In The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analogues, Suppl. E, Part 2; Wiley: Chichester, 1980, Chap. 20, 881-902.
  • 41
    • 34548720959 scopus 로고    scopus 로고
    • Typical Procedure for o-Benzenedisulfonimide-Catalyzed Etherification (Entry 1, Table 1) To a solution of 1,3-diphenylprop-2-en-1- ol (3; 0.42 g, 2.0 mmol) in abs. EtOH (10 mL) was added o-benzenedisulfonimide (1; 5 mol, 0.02 g, 0.1 mmol, the reaction mixture was stirred at r.t. The reaction was monitored by TLC (PE-Et 2O, 6:4, GC, and GC-MS analyses until complete disappearance of the starting material. Then the reaction mixture was evaporated under reduced pressure and the residue was poured into Et2O-H2O (40 mL, 1:1, The aqueous layer was separated. The organic extract was washed with H2O (20 mL, dried over Na2SO4, and evaporated under reduced pressure. The crude residue was chromatographed on a short column (PE-Et2O, 6:4) to provide pure (E)-1,3-diphenyl-3-ethoxyprop- 1-ene (4a; GC, GC-MS, TLC, 1H NMR) in 77% yield 0.37 g, colorless oil
    • +], 105 (100).
  • 42
    • 34548800287 scopus 로고    scopus 로고
    • Typical Procedure for o-Benzenedisulfonimide-Catalyzed Esterification (Entry 5, Table 1) To a solution of phenylacetic acid (5; 0.27 g, 2.0 mmol) and butan-1-ol (0.16 g, 2.2 mmol) in toluene (10 mL) was added o-benzenedisulfonimide (1; 25 mol, 0.11 g, 0.5 mmol) and the reaction mixture was stirred at 90°C for 30 min. After the usual workup, the crude residue was chromatographed on a short column (PE-Et2O, 8:2) to provide pure butyl phenylacetate (6a; GC, GC-MS, TLC, 1H NMR) in 90% yield (0.38 g, colorless oil with spectral data identical to those reported.22d 1H NMR: δ, 0.85 (t, J, 7.0 Hz, 3 H, 1.23-1.34 (m, 2 H, 1.48-1.58 (m, 2 H, 3.56 (s, 2 H, 4.04 (t, J, 6.6 Hz, 2 H, 7.15-7.28 (m, 5 H, 13C NMR: δ, 13.86, 19.27, 30.80, 41.66, 64.94, 127.21, 128.72 (2 C, 129.43 (2 C, 134.40, 171.88; MS (EI, 70 eV, m/z, 192 5, M
    • +], 91 (100).
  • 43
    • 34548705396 scopus 로고    scopus 로고
    • Typical Procedure for o-Benzenedisulfonimide- Catalyzed Acetalization (Entry 10, Table 1) To a solution of 4-chlorobenzaldehyde (7a; 0.28 g, 2 mmol) and ethane-1,2-diol (9; 0.37 g, 6 mmol) in toluene (5 mL) was added o-benzenedisulfonimide (1; 1 mol, 0.0044 g, 0.02 mmol) and the reaction mixture was stirred at 90°C for 60 min. The reaction mixture was treated with solid NaHCO 3, evaporated under reduced pressure, and the residue was poured into Et2O-H2O (40 mL, 1:1, The aqueous layer was separated. The organic extract was dried over Na2SO4, and evaporated under reduced pressure; the crude residue was chromatographed on a short column (PE-Et2O, 9.5:0.5) to provide pure 4-chlorobenzaldehyde ethlylene acetal in 87% yield (8d; 0.32 g, colorless oil with spectral data identical to those reported.19b 1H NMR: δ, 3.92-3.99 m, 2 H, 4.02-4.09
    • +], 183 (100).
  • 45
    • 34548810825 scopus 로고    scopus 로고
    • The aqueous layer and aqueous washing from the various reactions were collected and evaporated under reduced pressure. The residue was passed through a column of Dowex 50X8 ion-exchange resin (1.6 g for 1 g of product, eluting with H2O (about 35 mL, After removal of H2O under reduced pressure, virtually pure (1H NMR) o-benzenedisulfonimide(1) was recovered; mp 192-194°C, from toluene lit. 3: mp 192-194°C
    • 1H NMR) o-benzenedisulfonimide(1) was recovered; mp 192-194°C, from toluene (lit. 3: mp 192-194°C).
  • 47
    • 85127181128 scopus 로고    scopus 로고
    • For compound 6a, see: (a) Sharghi, H.; Sarvari, M. H.; Eskandari, R. J. Chem. Res., Synop. 2005, 488.
    • For compound 6a, see: (a) Sharghi, H.; Sarvari, M. H.; Eskandari, R. J. Chem. Res., Synop. 2005, 488.
  • 50
    • 0041334074 scopus 로고    scopus 로고
    • For compounds 6a and 6b, see: Gumaste, V. K.; Deshmukh, A. R. A. S.; Bhawal, B. M. Indian J. Chem., Sect. B: Org. Chem. Inch Med. Chem. 1996, 35, 1174.
    • (d) For compounds 6a and 6b, see: Gumaste, V. K.; Deshmukh, A. R. A. S.; Bhawal, B. M. Indian J. Chem., Sect. B: Org. Chem. Inch Med. Chem. 1996, 35, 1174.
  • 51
    • 2942538207 scopus 로고    scopus 로고
    • For compounds 8a and 8b, see: (a) Shimizu, K.-I.; Hayashi, E.; Hatamachi, T.; Kodama, T.; Kitayama, Y. Tetrahedron Lett. 2004, 45, 5135.
    • For compounds 8a and 8b, see: (a) Shimizu, K.-I.; Hayashi, E.; Hatamachi, T.; Kodama, T.; Kitayama, Y. Tetrahedron Lett. 2004, 45, 5135.
  • 52
    • 30844447201 scopus 로고    scopus 로고
    • For compound 8d, see: (b) Azzena, U.; Dettori, G.; Sforazzini, G.; Yus, M.; Foubelo, F. Tetrahedron 2006, 62, 1557.
    • For compound 8d, see: (b) Azzena, U.; Dettori, G.; Sforazzini, G.; Yus, M.; Foubelo, F. Tetrahedron 2006, 62, 1557.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.