Heterocycles by Cycloaddition. Part 9. Bridged Heteroannulenes by Cycloaddition-Extrusion-Ring-expansion Reactions of Mesoionic Compounds with Benzocyclopropene. A Methanothiazonine, a Methanothionine, and a Methanothiecinone
A methanothiazonine (13) was formed by cycloaddition-extrusion-ring expansion of benzocyclopropene with a mesoionic oxathiazoliumolate (12).The reaction with a dithioliumolate (14) gave the cycloadduct (15), from which a methanothionine (16) and a methano
PREPARATION OF SOME STABLE AND TRANSIENT 1,3-OXAZOLIUM-4-OLATES
A number of mandelanilides (6) were prepared and oxidized with barium manganate to phenylglyoxanilides (7).The latter were converted to N-benzoylglyoxanilides which, upon heating with triethyl phosphite, gave the corresponding 1,3-oxazolium-4-olates (2).
Haddadin, Makhluf J.,Tannus, Hana T.
p. 773 - 778
(2007/10/02)
Novel Synthesis of the Mesoionic System 1,3-Oxazolium-4-olate
Thermolysis or photolysis of N-phenyldibenzoylnitrone (1) produces N-benzoylphenylglyoxanilide (5) and not the previously reported oxaziridine 2.Treatment of imide 5 with triethyl phosphite produced 2,3,5-triphenyl-1,3-oxazolium-4-olate (8), a new member
Haddadin, Makhluf J.,Kattan, Asma M.,Freeman, Jeremiah P.
p. 723 - 725
(2007/10/02)
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