Competitive anion formation in pulegone [p-menth-4(8)-en-3-one] synthesis of phenylmethylenepyrans

Crabbe, Patricia; Diaz, Eduardo Mateos; Haro, J.; Pérez, G.; Salgado, David Cienfuegos; Santos, Estela

doi:10.1039/p19720000046

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1987

2003

Publication Types

Select...

Book2

Article1

Other1

Relationship

Self Cite0

Independent4

Authors

Journals

Cited by 4 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The extract was washed with sat. NaCl s o h , dried, and evaporated, leading to 5.30 g (20% overall yield) of 3c [6]. M.p.…”

mentioning

confidence: 99%

Synthesis of 2‐Cycloalkenones (Parts of 1,4‐Diacyl‐1,3‐butadiene Systems) and of a Heterocyclic Analogue by Metal‐Catalyzed Decomposition of 2‐Diazoacylfurans

Wenkert

Guo

Pizzo

et al. 1987

Helvetica Chimica Acta

View full text Add to dashboard Cite

Furans with side-chains at C(2) of various lengths terminating in diazomethyl keto groups are shown to undergo Rh*(OAc),-catalyzed furan unravelling with the production of 2-cyclopentenone, 2-cyclohexenone, and 2-cycloheptenone to each of whose olefinic C(p) is attached an acrylaldehyde unit. Interposition of a cyclohexane or a methylaminomethylene moiety between the furan and diazoketo functions leads to the formation of a hydroindenone and pyrrolone, respectively. Replacement of the diazomethylketo terminus by an cc-diazoethylketo system or a a-diazo-b-keto-ester function produces 2-substituted 2-cycloalkenones. A furan with a C,, diazomethylketo-terminating side-chain at C(3) is described to be transformed into a 4-formylmethylidene-2-cyclohexenone.Introduction. -In a recent, broad study of the decomposition of ethyl diazoacetate,

show abstract

“…The extract was washed with sat. NaCl s o h , dried, and evaporated, leading to 5.30 g (20% overall yield) of 3c [6]. M.p.…”

mentioning

confidence: 99%