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Rearrangement of [1-2H]- and [2-2H]naphthalene 1,2-oxides to 1-naphthol. Mechanism of the NIH shift

✍ Scribed by Boyd, D. R.; Daly, J. W.; Jerina, D. M.

Book ID
127290672
Publisher
American Chemical Society
Year
1972
Tongue
English
Weight
640 KB
Volume
11
Category
Article
ISSN
0006-2960

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## Abstract Heating of 1′‐(__N__‐substituted carbamoyl)methylspiro[2__H__‐1‐benzopyran‐2,2′‐[2__H__]indoles] with potassium hydroxide in ethanol yields diastereomeric 5a,13‐methano‐6__H__‐1,3‐benzoxazepino[3,2‐__a__]indole‐12‐carbox‐amides. Reduction of the latter with sodium borohydride affords 1,