Abstract: 1. A study was made of the dependence of the lactonization reaction on steric structure for all four isomeric 1,2,3,5,6,7,8,8a-octahydro-1,2-naphthalenedicarboxylic acids (I), (X), (XIII), and (XIX). 2. It was shown that the syn-cis dicarboxylic acid (I) and the syn-traps dicarboxylic acid (X) are lactonized to the corresponding isomeric γ-lactone acids (II) and (XI), which contain γ-lactone rings. The acid (X) is lactonized considerably less readily than the isomeric acid (II). 3. Lactonization of the anti-cis dicarboxylic acid (XIII) proceeds with difficulty and gives a mixture of the chloro dicarboxylic acid (XV) and the anti-cis S-lactone (XIV), the structure of which, as a σ-lactone acid, was confirmed by various chemical reactions and by the infrared spectrum. The anti-traps dicarboxylic acid (XIX) was found to be quite incapable of lactonization. 4. It was shown that, as a result of double-bond displacement, the isomeric syn-cis and anti-cis dicarboxylic acids (I) and (XIII) give the same cis-dicarboxylic acid (VIII), which has an intercycle double bond, this being further confirmation of our previous results on the configurations of the acids (I) and (XIII) as epimers with respect to hydrogen at C-8a. 5. The stereochemical peculiarities of the lactonization of the isomeric, 1,2,3,5,6,7,8,8a-octahydro-1,2-naphthalenedicarboxylic acids as a function of their spatial configurations were examined and explained with the aid of molecular models.

Cite: Nazarov I.N. , Kucherov V.F. , Andreev V.M.
Stereochemistry of cyclic compounds. Communication 12. Stereochemistry of lactones of 1,2,3,5,6,7,8,8a-octahydro-1,2-naphthalenedicarboxylic acids
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1956. V.5. N8. P.971-978. DOI: 10.1007/bf01166412 OpenAlex

Identifiers:

OpenAlex:

W4236199194

Citing: Пока нет цитирований

Altmetrics: