Stable Quinone Methides: Regioselective  para ‐Oxidation of a 2,4‐bis[(alkylthio)methyl]phenol and addition reactions to quinonemethides | Zendy

Meier Hansrudolf | Zendy; Kuenzi Hanspeter | Zendy; Fuhrer Hermann | Zendy; Rist Günther | Zendy

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Stable Quinone Methides: Regioselective para ‐Oxidation of a 2,4‐bis[(alkylthio)methyl]phenol and addition reactions to quinonemethides

Author(s) -

Meier Hansrudolf,

Kuenzi Hanspeter,

Fuhrer Hermann,

Rist Günther

Publication year - 1994

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19940770308

Subject(s) - chemistry , regioselectivity , benzaldehyde , potassium ferricyanide , phenol , dehydrogenation , hydrolysis , medicinal chemistry , organic chemistry , nuclear magnetic resonance spectroscopy , catalysis

The 2,4‐bis‐functionalized phenol 1 is dehydrogenated regioselectivity with potassium ferricyanide, affording the corresponding p ‐quinonemethide 2 . Hydrolysis of 2 affords a mixture of dithioacetal 5a and benzaldehyde 6 ; 1,6‐addition of thiols to 2 gives the dithioacetals 5 of benzaldehyde 6 ; reaction of 2 with 2,2′‐azobis(isobutyronitrile) (= 2,2′‐dimethyl‐2,2′‐azobis(propanenitrile)) leads to 9a, 9b , and 10 , addition products of the 1‐cyano‐1‐methylethyl radical. The structures of all products are confirmed mainly by 1 H‐ and 13 C‐NMR spectroscopy, and the mode of their formation is discussed.

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