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ABRAMOV PHOSPHORYLATION

ABRAMOV PHOSPHORYLATION REACTION

ABRAMOV PHOSPHORYLATION DISCONNECTION

ABRAMOV PHOSPHORYLATION MECHANISM

 

NOTES : 

The O-benzylated glycal is oxidatively cleaved to the aldehyde sugar bearing a formate ester at C-5. This carbon atom is originally the anomeric carbon atom. The condensation with trimethyl phosphite in glacial acetic acid or with dimethyl phosphonate under basic conditions introduces the dimethylphosphonyl moiety. See also Arbuzov (Michaelis – Arbuzov), Michaelis – Becker – Nylén and Perkow reactions. 

ACHMATOWICZ PYRANONE REACTION

ACHMATOWICZ PYRANONE REACTION

ACHMATOWICZ PYRANONE MECHANISM

ACHMATOWICZ PYRANONE DISCONNECTION

NOTES : 
The synthesis of pyran-3-ones starting with furfuryl alcohols, which are first converted to dialkoxydihydrofurans by e.g.Clauson–Kaas electrochemical oxidation, followed by acid hydrolysis. There is also an aza-analogue known based  on furylacetamides. See also Clauson–Kaas reaction.

ADAMS DECARBOXYLATION REACTION


ADAMS DECARBOXYLATION REACTION

ADAMS DECARBOXYLATION DISCONNECTION

ADAMS DECARBOXYLATION MECHANISM

NOTES : 
Coumarin acids (2-oxo-2H-chromene-3-carboxylic acid) are decarboxylated by heating with aqueous sodium hydrogensulfite followed by treatment with concentrated alkali or acid. 

ADKINS – PETERSON FORMALDEHYDE REACTION

ADKINS – PETERSON FORMALDEHYDE REACTION

NOTES : 
An air methanol mixture, containing 5 – 8 % methanol vapour is passed over a metal oxide (Iron oxide, molybdenum oxide or iron molybdenum oxide) catalyst to afford 40% aqueous formaldehyde free of methanol. 

ADLER – LONGO PORPHYRIN REACTION

ADLER – LONGO PORPHYRIN DISCONNECTION

ADLER – LONGO PORPHYRIN MECHANISM

ADLER – LONGO PORPHYRIN REACTION

NOTES : 
This is a very low yielding and slow reaction for the formation of porphyrins. Several improved syntheses have been published over the years. See also Lindsey, MacDonald, Rothemund and Taniguchi reactions. 

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