Sigmatropic Rearrangement of Ammonium Ylides—Key Step in the Synthesis of Methyl 2-Formylphenyl Acetate
Anna Kowalkowska , Andrzej Jończyk
AbstractN-Cyanomethyl-N,N-dimethyl-N-(a-methoxycarbonyl)benzylammonium salts 5 were synthesized and treated with different base / solvent systems, giving the products of sigmatropic rearrangements [2,3] 7 and [1,2] 8. In reactions carried out in liquid ammonia, [2,3] rearrangement definitively prevailed. Pure 7(or mixture of 7 and 8) were deprotected to afford methyl 2-formylphenyl acetate (9) in good yield.
|Journal series||Synthetic Communications, ISSN 0039-7911, (A 20 pkt)|
|Keywords in English||Ammonium salts; ammonium ylides; methyl 2-formylphenyl acetate; sigmatropicrearrangement|
|Publication indicators||= 6; = 6; : 2014 = 0.462; : 2011 = 1.062 (2) - 2011=1.091 (5)|
|Citation count*||4 (2015-03-19)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.