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Cationic oligomerization of bicyclic oxalactam

✍ Scribed by Hashimoto, Kazuhiko ;Sumitomo, Hiroshi

Book ID
105335247
Publisher
John Wiley and Sons
Year
1984
Weight
417 KB
Volume
22
Category
Article
ISSN
0360-6376

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✦ Synopsis

Abstract

Cationic oligomerization of bicyclic oxalactam, 8‐oxa‐6‐azabicyclo[3.2.1]octan‐7‐one [abbreviated as BOL (1)], was carried out at 0–60°C with trifluoromethanesulfonic acid and borontrifluoride etherate as catalysts to obtain the oligomer mixture at high yield. From the structural analysis of the isolated dimer, a N‐(2(e)‐carbamoyltetrahydropyran‐6(e)‐yl)‐8‐oxa‐6‐azabicyclo[3.2.1]octan‐7‐one, the oligomerization proceeded through the ^5^C‐^6^N scission in (1) but not through the ^6^N‐^7^C (amide group) scission as generally observed in common lactams. This peculiar oligomerization must result from the protonation to the oxamide unit in the BOL molecule.

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