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The thio-Claisen rearrangements of allyl and propargyl 4-quinolyl sulfides

✍ Scribed by Yasuo Makisumi; Akira Murabayashi

Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
155 KB
Volume
10
Category
Article
ISSN
0040-4039

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✦ Synopsis

Earlier, we reported that the thio-Cloisen reorrongement of ally1 4quinolyl sulfides (I) to 2,3-dihydrothieno[3.2-clquinolines (III) proceeded through the prototropic cyclizotion of the initially formed 3-allyl-4(1 H)-quinolinethiones (II), on the basis of the quantitative transformation of II into III under mild conditions (1). I R=H, Me Recently, Kwart and Cohen (2) proposed a mechanism involving two possible intermediates, thiiron derivotive and o-methallylthiophenol for the thio-Cloisen rearrangement of methallyl phenyl sulfide.

πŸ“œ SIMILAR VOLUMES

The thio-Claisen rearrangement of allyl
The thio-Claisen rearrangement of allyl 4-quinolyl sulfides
✍ Yasuo Makisumi πŸ“‚ Article πŸ“… 1966 πŸ› Elsevier Science 🌐 French βš– 192 KB

It was reported in our previous papers (1) that, on heating at 2oo0, ally1 bquinolyl ethers were readily converted into the Claisen products, 3-allyl-4(1H)quinolones, in good yields accompanying small amounts of ring closure products, P,%dihydrofuro-[ 32-cjquinolines. H A ? or HBr-AcOH Several previ