Reaction of 1-azirines with 1,3-diphenylisobenzofuran. Ring expansion to isoquinoline, dihydroisoquinoline, and azanorcarane derivatives
Reaction of 1-azirines with 1,3-diphenylisobenzofuran. Ring expansion to isoquinoline, dihydroisoquinoline, and azanorcarane derivatives
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DOI：
10.1021/jo00980a033
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发表时间：
1972-07
影响因子：
3.6
通讯作者：
V. Nair
中科院分区：
文献类型：
--
作者：
V. Nair
5.8 Hz，1H）和在6.48和7.96之间的芳族区域中的多重峰（19 H，芳族）。根据下面讨论的光谱证据和化学转化，该化合物被指定为环加合物结构3。从其nmr光谱推断外立体化学，其显示氮丙啶氢（3.52）通过氧化桥的显著去屏蔽（> 1 ppm），这意味着该氢与氧是顺式的。Cava，9 Breslow，10 Battiste，11及其同事对环丙烯与1，3-二苯基异苯并呋喃加合物的研究进一步支持了这一任务。氮原子上的孤对电子-
5.8 Hz, 1 H) and multiplets in the aromatic region between 6.48 and 7.96 (19 H, aromatic). On the basis ofthe spectral evidence and the chem-ical transformations discussed below, the compound was assigned the cycloadduct structure 3. The exo stereo-chemistry was inferred from its nmr spectrum, which showed considerable deshielding (> 1 ppm) of the aziridine hydrogen (3.52) by the oxido bridge, implying that this hydrogen is syn to the oxygen. Further support for this assignment comes from work on cyclo-propene adductswith 1, 3-diphenylisobenzofuran by Cava, 9 Breslow, 10 Battiste, 11 and coworkers. The lone pair of electrons on the nitrogen of the cy-