DIPHENYLHYDROXYMETHYLATION OF 4-METHYLPYRIDINE N-OXIDE BY DIPHENYLKETYLS AND BENZHYDROL DIANIONS
The reaction of 4-methylpyridine N-oxide with lithium diphenylketyl gives the products from diphenylhydroxymethylation in the ring and in the side chain .The reaction with the potassium ketyl gives the product from diphenylhydroxymethylation in the ring and the analogous product from reductive diphenyl-hydroxymethylation .The reactions with the sodium ketyl and also with the dilithium, disodium, and dipotassium salts of the benzhydrol dianions give the product from substitution in the ring with significantly lower yields.
Turaeva, D. A.,Kurbatova, A. S.,Kurbatov, Yu. V.
p. 1323 - 1325
(2007/10/02)
Lewis Acid Complexed Heteroatom Carbanions; Synthesis of some α-Pyridyl Alcohols
Metallation of BF3-pyridine complex with lithium tetramethylpiperidide (LTMP) in ether at -78 deg C, followed by reaction with carbonyl compounds, affords α-pyridyl alcohols in good yields.
Kessar, Satinder V.,Singh, Paramjit,Singh, Kamal Nain,Dutt, Mahesh
p. 570 - 571
(2007/10/02)
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