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

✍ Scribed by Yung-Son Hon; Chia-Fu Lee

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 233 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00274-9

✦ Synopsis

Acetonyltriphenylphosphonium bromide (ATPB) is a precursor in the preparation of 1-(triphenylphosphoranylidene)-2-propanone used in a Wittig reaction. There are no reports on the use of ATPB in organic synthesis other than in ylide formation. 1 In the course of studying the counteranion effect on the reactivity of the phosphonium salt in the Wittig reaction, ATPB was found to be a catalyst in the trimerization of the aldehyde. 2 The trimerization occurred under neat conditions rather than in the solution (Scheme 1). We tried Scheme 1 0.1 eq. ATPB CH2C12, lh 38% O~...~O