The pummerer and the thio-claisen–type rearrangements of naphtho[1,8-bc]-1,5-dithiocin monooxide and N-p-tosylsulfilimine
✍ Scribed by Naomichi Furukawa; Hidetaka Shima; Satoshi Ogawa
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- English
- Weight
- 651 KB
- Volume
- 6
- Category
- Article
- ISSN
- 1042-7163
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✦ Synopsis
Naphtho[l,8-bc]-l,5-dithiocin
N-p-tosylsulfilirnine (8)
and rnonosulfoxide (9) were prepared. On treatment with conc. H,SO, both the sulfilirnine (8) and sulfoxide (9) gave the dithia dication which was converted to the sulfoxide by hydrolysis. The H-D exchange reaction of (8) took place highly regioselectively to afford the rnonodeuterated (8-D) at the a-position of the N-tosyl group. The Purnrnerer rearrangement reaction of monooxide (9) with acetic anhydride gave the a-acetoxy derivative by the dication (lob), while a new thio-Claisen rearrangement o f sulfilirnine (8) t- BuOK in CH,Cl, gave .Z'-allyl-naphtho[l, 8-bc]-1,5-dithiole.