Photochemistry of the Phthalimide System, 37. Thiazacycloalkanols by Photocyclization ofS-SubstitutedN-(Thioalkyl)phthalimides
β Scribed by Sato, Yasuhiko ;Nakai, Hideo ;Wada, Masao ;Mizoguchi, Tomishige ;Hatanaka, Yasumaru ;Migita, Yoshihiro ;Kanaoka, Yuichi
- Publisher
- John Wiley and Sons
- Year
- 1985
- Tongue
- English
- Weight
- 876 KB
- Volume
- 1985
- Category
- Article
- ISSN
- 0947-3440
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β¦ Synopsis
Abstract
NβSubstituted phthalimides (1, 2) possessing a terminal thioether function in their side chain were irradiated with a highβpressure mercury lamp to give a variety of thiazacycloalkanol derivatives (3, 7, 9β13, 16, 17) with favored Ξ³β, Ξ΄β, Ο΅β, and ΞΆβhydrogen abstractions (Table 1), in moderate to fairly good yields.
π SIMILAR VOLUMES
## Abstract __S__βSubstituted __N__β(thioalkyl)phthalimides 2 underwent photocyclization to give azathiacyclols, up to 16βmembered ring compounds, in good yields. The cyclization occurred between an imide carbonyl group and a terminal sulfide group located in a remote position from the carbonyl gro
Although photoreactions of amide groups have been well documented (l), very little is known about imide derivatives with the exception of photochemical additions to some maleimides (1). In N-substituted phthalimides the carbonyl groups as part of a strained five-membered ring system, are activated.
## Upon irradiation a homologous series of certain phthalimides (2a-c) possessing a -terminal sulfide function in their N-ply-ether side chain undergo regioselective remote photocyclization affording seven to fifteen-membered crown ether analogs (3a -c ) in nwderate yields.