Abstract
The product-selective electrolytic decarboxylation of γ-substituted paraconic acids has been studied (1) in dry methanol using sodium methoxide by addition of iron powder or ferric nitrate on platinum electrodes, (2) in dry methanol using sodium methoxide on carbon rod electrodes, and (3) in a mixed solvent of triethylamine-pyridine-water on carbon rod electrodes. Conditions 1 and 2 resulted in exclusive formation of 7-substituted butyrolactones in 80-99% yields, whereas condition 3 provided α,β-unsaturated butenolides in 70-90% yields. By means of the butenolide synthesis dl-3-carboxy-8-hydroxy-Δ3-menthene 7-lactone, a key intermediate for the preparation of dl-menthone, could be prepared.
| Original language | English |
|---|---|
| Pages (from-to) | 2486-2488 |
| Number of pages | 3 |
| Journal | Journal of Organic Chemistry |
| Volume | 39 |
| Issue number | 17 |
| Publication status | Published - 1974 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Electrolytic decarboxylation reactions. I. Electrosyntheses of γ-substituted butyrolactones and γ-substituted α,β-butenolides from γ-substituted paraconic acids. / Torii, Sigeru; Okamoto, Tsutomu; Tanaka, Hideo.
In: Journal of Organic Chemistry, Vol. 39, No. 17, 1974, p. 2486-2488.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Electrolytic decarboxylation reactions. I. Electrosyntheses of γ-substituted butyrolactones and γ-substituted α,β-butenolides from γ-substituted paraconic acids
AU - Torii, Sigeru
AU - Okamoto, Tsutomu
AU - Tanaka, Hideo
PY - 1974
Y1 - 1974
N2 - The product-selective electrolytic decarboxylation of γ-substituted paraconic acids has been studied (1) in dry methanol using sodium methoxide by addition of iron powder or ferric nitrate on platinum electrodes, (2) in dry methanol using sodium methoxide on carbon rod electrodes, and (3) in a mixed solvent of triethylamine-pyridine-water on carbon rod electrodes. Conditions 1 and 2 resulted in exclusive formation of 7-substituted butyrolactones in 80-99% yields, whereas condition 3 provided α,β-unsaturated butenolides in 70-90% yields. By means of the butenolide synthesis dl-3-carboxy-8-hydroxy-Δ3-menthene 7-lactone, a key intermediate for the preparation of dl-menthone, could be prepared.
AB - The product-selective electrolytic decarboxylation of γ-substituted paraconic acids has been studied (1) in dry methanol using sodium methoxide by addition of iron powder or ferric nitrate on platinum electrodes, (2) in dry methanol using sodium methoxide on carbon rod electrodes, and (3) in a mixed solvent of triethylamine-pyridine-water on carbon rod electrodes. Conditions 1 and 2 resulted in exclusive formation of 7-substituted butyrolactones in 80-99% yields, whereas condition 3 provided α,β-unsaturated butenolides in 70-90% yields. By means of the butenolide synthesis dl-3-carboxy-8-hydroxy-Δ3-menthene 7-lactone, a key intermediate for the preparation of dl-menthone, could be prepared.
UR - http://www.scopus.com/inward/record.url?scp=1542662695&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=1542662695&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:1542662695
VL - 39
SP - 2486
EP - 2488
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 17
ER -