Opening book details…
Can I read The vinylogous conia rearrangement: A masked ene reaction on EtoBox?
The vinylogous conia rearrangement: A masked ene reaction by Andrew S Kende; Ronald C Newbold is a Chemistry article available to read on EtoBox.
What is The vinylogous conia rearrangement: A masked ene reaction about?
## A novel carbocyclic thermal rearrangement of 4-subsdruted 2-cyclohexen-1 -ones is suggested 10 involve a inasked ene reaction andprovides afacile route to spirocyclrc cyclohexenone systems. The thermal cyclization of unsaturated carbonyl compounds, or Conia reaction, is a useful means of generating rings a to an aldehyde or ketone.l A shortcoming of this reaction has been that an olefin is the maximum functionality produced in the newly formed ring. We have recently described a general route to bicyclic keto-silanes by the thermal rearrangement of P-substituted silylacetylenic cycloalkanoncs, a variant which should greatly enhance the utility of this process.\* ## 285 'C TMS H We now report a hitherto unknown thermal rearrangement which results in the formation of spirocyclic enones upon heating certain y-substituted a$-unsaturated cyclic kctones.3 A summary of our findings is given in the Table .4 Formally thcsc transformations corrcspond to "vinylogous" Conia rearrangements. Yields for these reactions are moderate to good (48-72%), and in the cyclization of 1 a single diastereomer was formed, shown by nOe studies to have the methyl u to the enone double bond.5 These reactions
Who reads The vinylogous conia rearrangement: A masked ene reaction?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- Andrew S Kende; Ronald C Newbold
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)
- Published
- 1989
- Language
- EN
- Field
- Chemistry (Physical Sciences)