Acetonyltriphenylphosphonium bromide in organic synthesis: An extremely efficient catalyst for the protection and deprotection of alcohols as alkyl vinyl ethers

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2389-2392

  Hon, Yung Son ^a   Lee, Chia Fu ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONYLTRIPHENYLPHOSPHONIUM BROMIDE; ALCOHOL DERIVATIVE; ETHER DERIVATIVE; PHENOL; PHOSPHONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; SYNTHESIS;

EID: 0033583295     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00274-9     Document Type: Article

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42. 2 was added ATPB (29.7 mg, 0.07 mmol) and the solution was stirred at RT. The reaction was complete in 5 min. The solution was concentrated and chromatographed on silica gel to give the desired product 6a (315.8 mg, 0.67 mmol) in 91% yield.
43. 2 was used as a cosolvent. Only MeOH was used in the other cases.) The solution was concentrated and chromatographed on silica gel to give the desired product 6 (54 mg, 0.14 mmol) in 99% yield.
44. 16. If p-toluenesulfonic acid was used as catalyst in the reaction, the major product is 1-phenylcyclohexene (86% yield) and the THP ether 7a was formed in 2% yield only.
45. 17. If p-toluenesulfonic acid was used as catalyst in the reaction, complex mixtures were formed, as indicated by TLC and the THP ether 10a was isolated in 40% yield.
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48. 20. PPTS is an excellent reagent for the the preparation and deprotection of THP ethers (see ref. 4d) However, it is quite hydroscopic. ATPB is much less hydroscopic than PPTS.