Email this article Products of reaction of 1-phenyltricyclo[4.1.0.02,7]heptane with N-iodosuccinimide in aqueous THF
- Authors: Vasin V.A.1, Romanova E.V.1, Razin V.V.2
-
Affiliations:
- Ogarev Mordovia State University
- St. Petersburg State University
- Issue: Vol 53, No 11 (2017)
- Pages: 1749-1752
- Section: Short Communications
- URL: https://bakhtiniada.ru/1070-4280/article/view/216987
- DOI: https://doi.org/10.1134/S1070428017110252
- ID: 216987
Cite item
Open Access
Access granted
Subscription Access
Abstract
Iodohydroxylation of 1-phenyltricyclo[4.1.0.02,7]heptane in aqueous THF at 20°C with N-iodosuccinimide proceeds at the central bicyclobutane bond C1–C7 and results in the formation of two-component mixture of diastereomeric 7-iodo-6-phenyl-6-norpinanols in the ratio 1 : 1.8 in favor of the product of the anti-addition. Treating of iodonorpinanols with trimethylamine in aqueous THF affords 1-benzoylcyclohex-1-ene as a result of 1,4-dehydroiodination accompanied with the Grob fragmentation of the carbon scaffold.
About the authors
V. A. Vasin
Ogarev Mordovia State University
Author for correspondence.
Email: vasin@mrsu.ru
Russian Federation, Bol’shevistskaya ul. 68, Saransk, 430005
E. V. Romanova
Ogarev Mordovia State University
Email: vasin@mrsu.ru
Russian Federation, Bol’shevistskaya ul. 68, Saransk, 430005
V. V. Razin
St. Petersburg State University
Email: vasin@mrsu.ru
Russian Federation, St. Petersburg
Supplementary files
