Untitled

J. Polym. Sci. Polym. Chem. Ed.

1984

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SynopsisCationic oligomerization of bicyclic oxalactam, 8-oxa-6-azabicyclo[3.2.l]octan-7-one [abbreviated as BOL (111, was carried out at 04WC 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(ekarbamoyltetrahydropyran-6(e )-yl)-8-oxa-6azabicyclo[3.2.l]octan-7-one, the oligomerization proceeded through the G 6 N scission in (1) but not through the 6N-7C (amide group) scission as generally observed in common lactams. This peculiar oligomerization must result from the protonation to the oxamide unit (--O--CH--NH4=0) in the BOL molecule. I I

“…Calcd for GHllN02: C, 59.55%; H, 7.86%; N, 9.92%. Found: C, 59.63%; H, 7.88%; N, 9.87%. Oligomerization BOL (1) was dried and stored over phosphorus pentoxide in U~C U O until used.…”

Section: N-methyl-8-oxa-6-azabicyclo[32l]octan-7-0ne (6)mentioning

confidence: 99%

Cationic oligomerization of bicyclic oxalactam

J. Polym. Sci. Polym. Chem. Ed.

1984

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Preparation of block- and graft copolymers starting from a bicyclic oxalactam

1985

Makromol. Chem.

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A new block copolymer composed of hydrophilic polyamide as outer segments and polyoxyethylene as an inner segment was obtained by anionic polymerization of a bicyclic oxalactam, 8-oxa-6-azabicyclo[3.2.l]octan-7-one, using the isocyanate-terminated polyoxyethylene as an activator. benzyl end group was prepared by anionic polymerization of the bicyclic oxalactam followed by the reaction with p-vinylbenzylamine. Its radical copolymerization with styrene was conducted to obtain a graft copolymer consisting of a nonpolar hydrophobic polystyrene stock and hydrophilic polyamide branches.

Isomerization of polyamide prepared from bicyclic oxalactam

J. Polym. Sci. Polym. Chem. Ed.

1983

Anionic solution polymerization of bicyclic oxalactam, 8‐oxa‐6‐azabicyclo[3.2.1]octan‐7‐one (abbreviated as BOL), at 25°C yields the polyamide with both carbonyl and imino groups at the axial positions in the tetrahydropyran ring. On the other hand, the polyamide obtained by bulk anionic polymerization of BOL at 100°C has more complicated structures, probably due to the isomerizations and side reactions. The most frequent isomerization of the polyamide was the transfer of the carbonyl group adjacent to the tetrahydropyran ring from the equatorial to the axial position in the presence of base or acid catalyst at 25°C. Mechanisms are discussed from the viewpoint of the characteristic bonds in the polyBOL chain.