Stable alpha-methoxy arylmethyl carbanions can be generated by metalation of arylmethyl methyl ethers, 1, with n-BuLi in THF at -40 degrees C, avoiding Wittig rearrangement to the corresponding alkoxides 2. Reaction of these carbanions with various electrophiles afforded the expected products 3 in satisfactory yields. Connection between the metalation procedure and the reductive electrophilic substitution of arylmethyl methyl ethers allowed the transformation of compounds 1 into 2-arylpropanoic acids, 5
METALATION OF ARYLMETHYL METHYL ETHERS AND CONNECTION WITH THEIR REDUCTIVE ELECTROPHILIC SUBSTITUTION / Azzena, Ugo Gavino; S., Demartis; M. G., Fiori; G., Melloni; Pisano, Luisa. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 36:31(1995), pp. 5641-5644. [10.1016/0040-4039(95)01035-G]
METALATION OF ARYLMETHYL METHYL ETHERS AND CONNECTION WITH THEIR REDUCTIVE ELECTROPHILIC SUBSTITUTION
AZZENA, Ugo Gavino;PISANO, Luisa
1995-01-01
Abstract
Stable alpha-methoxy arylmethyl carbanions can be generated by metalation of arylmethyl methyl ethers, 1, with n-BuLi in THF at -40 degrees C, avoiding Wittig rearrangement to the corresponding alkoxides 2. Reaction of these carbanions with various electrophiles afforded the expected products 3 in satisfactory yields. Connection between the metalation procedure and the reductive electrophilic substitution of arylmethyl methyl ethers allowed the transformation of compounds 1 into 2-arylpropanoic acids, 5I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
