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Intramolecular reactions of nitroolefin-β-diketone Michael adducts by Arnold T. Nielsen; T.G. Archibald is a Chemistry article available to read on EtoBox.

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1.3-Cycloheianedione (3) undergoes Michael addition to jS-nitrostyrene in methanolic sodium methoxide to form 3,5dioxo-4-phenyl-2,3,5,6,7,8-hexahydro-4H-l,Zbenzoxazine (!!a). With l-nitropropene 3 forms the corresponding Qmethyl derivative (Sb). These substances had been designated as Csubstituted 5-oxo-5.6.7.8-tetrahydro-4H-l.2-benzoxazine-2-oxides (4a, b) by other workers. 5,5-Dimethyl-1.3cyclohexanedione (9) under similar conditions adds to 8-nitrostyrene to form 2-(2-nitro-lphenylethyl)-5,5dimethyl-1,3cyclohexanedione (10); 9 and 2-nitro-l-phenylpropene yield 3-phenyl-2,6,6 trimethyl-6,7dihydro-4(5If)-benxofuranone (12). In other reactions various f3diketones add to nitroolefins to yield normal Michael adducts, Cnitro-I-alkanona (1, 2). Molecular ion fragmentation patterns and mechanisms of formation of the abnormal addition products are presented and their rationalizations discussed. MICHAEL addition of a variety of pdiketones to nitroolefins usually occurs in a normal manner to yield 1: 1 adducts, Cnitro-1-alkanones (1);re6 j!Lketo esters behave similarly.4v '-' P-Diketones previously employed in these additions include acyclic (RCO),CH2 + R'CH=C(R")N02 BL. (RCO),CHCH(R')CH(R

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Author

Arnold T. Nielsen; T.G. Archibald

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1969

Language

EN

Field

Chemistry (Physical Sciences)