SYNTHESES AND REACTIONS OF 3-PHENYLOXETE AND THE PARENT UNSUBSTITUTED OXETE
SYNTHESES AND REACTIONS OF 3-PHENYLOXETE AND THE PARENT UNSUBSTITUTED OXETE
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DOI：
10.1021/jo00315a016
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发表时间：
1981-01-01
影响因子：
3.6
通讯作者：
LAM, PYS
中科院分区：
文献类型：
--
作者：
FRIEDRICH, LE;LAM, PYS
从取代氧杂环烷中消除对甲苯磺酸和邻硝基苯基亚硒酸，分别得到3-苯氧基(6)和邻硝基苯基亚硒酸(9)。3-苯氧基(6)经历了预期的化学以及三重态氧的简单加成，得到了苯酰甲酸酯(10)。在室温下，母体OXETE(9)在溶液中的热半衰期为~8h。文献中已假定OXETE(9)在许多类型的反应中是活性中间体。1在大多数情况下，氧化剂对烯酮的裂解是不稳定的。尽管含氟氧化物相当稳定，但未含氟氧化物的热稳定性有限。在两个案例中，我们能够制备无氟氧化物
The eliminationof p-toluenesulfonic acid and o-nitrophenylselenilic acid from substituted oxetanes gives 3-phenyloxete (6) and oxete (9), respectively. 3-Phenyloxete (6) undergoes the expected chemistry as well as a facile additionof triplet oxygen to give phenacyl formate (10). The parent oxete (9) has a thermal half-life in solution at room temperature of~ 8 h.Oxetes have been postulated as reactive intermediates in many types of reactions in the literature. 1 In most cases, the oxetes were unstable toward fragmentation to enones. Even though fluorinated2 3oxetes are quite stable, unfluorinated oxetes have only limited thermal stability. In two cases, we were able to prepare unfluorinated oxetes