Aldehydes by Formylation of Grignard or Organolithium Reagents with N-Formylpiperidine

✍ Scribed by Prof. Dr. George A. Olah; Mr. Massoud Arvanaghi

• Publisher: John Wiley and Sons
• Year: 1981
• Tongue: English
• Weight: 262 KB
• Volume: 20
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198108781

✦ Synopsis

dence for the rearrangement (2)+( 7). However, this isomerization can also be detected when (la) is used as starting material: Thus, on reaction of (la) with 6 equivalents of potassium tert-butoxide in THF at 35"C, the enol ether (10) is obtained in 44% yield. Its formation can be explained in terms of the rearrangement (2)-+( 7) and subsequent addition of tert-butoxide to the reactive double bond C2-C3 of (7). On addition of anthracene to the system (la)/ KO-tBu/THF and elevation of the temperature to 65 "C, ( 6 4 is formed as well as (SQ) and (l0)ls1.

Chem. 43. 242 (1978)) uia metalation at position 7 by n-hutyllithium and reaction of the organometallic intermediate with p-toluenesulfonyl bromide (G.