Dependence of the steric selectivity of the mercuration of the dimethyl ester of tricyclo[4.2.2.o2,5]deca-3,7-diene-cis-endo-9,10-dicarboxylic acid on the solvent
โ Scribed by V. R. Kartashov; I. N. Sokolova; E. V. Skorobogatova; Yu. K. Grishin; D. V. Bazhenov; V. A. Roznyatovskii; A. S. Koz'min; N. S. Zefirov
- Book ID
- 112448427
- Publisher
- Springer
- Year
- 1987
- Tongue
- English
- Weight
- 67 KB
- Volume
- 36
- Category
- Article
- ISSN
- 1573-9171
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## Abstract Acid treatment of 9__exo__โmethylโ__anti__^10,11^โtricyclo[4.2.1.1^2,5^]decaโ3,7โdieneโ9__endo__, 10__endo__โdiol (**8**) leads to the two isomeric pentacyclic ethers **7** and **9** by intramolecular nucleophilic substitution of a protonated OHโgroup with participation of a C,Cโdouble
The acid cataZysed rearrangement of to 2a is shown to proceed through concommitant eLectrophiZic and nucleophilic -attack on an alkene by an incipient carbonium ion and the remaining aZcoho2 function.
## Abstract Racemic 4,8โdimethylโ1โoxaspiro[4.5]decaโ3,7โdienโ2โone (andirolactone) (1) was synthesized in two steps with 58% overall yield, starting from 4โmethylโ3โcyclohexenone (2) and methyl propynoate (3).