Molecular sieves as an efficient and recyclable catalyst for bromolactonization and bromoacetoxylation reactions

Tetrahedron Letters

Volumn 51, Issue 26, 2010, Pages 3433-3435

  Chen, Feng ^a   Jiang, Xiaojian ^a   Er, Jun Cheng ^a   Yeung, Ying Yeung ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

4 PENTENOIC ACID; ACID; ALKENE; CHEMICAL AGENT; HALOGEN; MOLECULAR SIEVE; N BROMOSUCCINIMIDE; UNCLASSIFIED DRUG;

ARTICLE; BROMOACETOXYLATION; BROMOLACTONIZATION; CATALYSIS; CATALYST; CHEMICAL REACTION; LACTONIZATION; REACTION ANALYSIS;

EID: 77953232274     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.113     Document Type: Article

References (17)

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9. The molecular sieves were purchased from Aldrich and used as received without further treatment. Molecular sieves from other companies including Alfa and Acros worked equally well.
10. 2 to recover the molecular sieves. The combined filtrate was concentrated under reduced pressure. The white solid paste obtained was diluted with n-hexanes (10 mL), filtered, and concentrated under reduced pressure to give lactone 2 (178 mg, 99%). The residue was dried to yield succinimide (121 mg, 99%).
11. The longer reaction time was due to the unoptimized rate of stirring the suspension.
12. A shaker was used instead of a magnetic stirrer as the reaction suspension was sticky.
13. Ranganathan S., Muraleedharan K.M., Vaish N.K., and Jayaraman N. Tetrahedron 60 (2004) 5273-5308
14. Garnier J.M., Robin S., and Rousseau G. Eur. J. Org. Chem. 20 (2007) 3281-3291
15. All the products were characterized and the physical data were in full accordance with literature values.
16. pH values were measured by stirring the suspension of molecular sieves in water for 10 min before testing using pH paper.
17. Preliminary results indicated that 5 Å MS catalyzed the bromoetherification of 4-penten-1-ol in 66% yield.