Synthesis of Hydroxy Group-Containing Poly(N-Propargylamides): Examination of the Secondary Structure and Chiral-Recognition Ability of the Polymers

✍ Scribed by Fumio Sanda; Toru Fujii; Junichi Tabei; Masashi Shiotsuki; Toshio Masuda

• Book ID: 102484666
• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 216 KB
• Volume: 209
• Category: Article
• ISSN: 1022-1352
• DOI: 10.1002/macp.200700374

✦ Synopsis

Abstract

Optically‐active, novel N‐propargylamides bearing hydroxy groups: (S)HCCCH~2~NHCOCH(CH~3~)OH (1), (S)HCCCH~2~NHCOCH(CH~3~)CH~2~OH (2), (S)HCCCH~2~NHCOCH[CH(CH~3~)~2~]OH (3), (S)HCCCH~2~NCOCH[CH~2~CH(CH~3~)~2~]OH (4), (S)HCCCH~2~NHCOCH(C~6~H~5~)OH (5), and (S)HCCCH~2~NHCOCH(CH~2~C~6~H~5~)OH (6) were synthesized and polymerized with [(nbd)RhCl]~2~–Et~3~N as a catalyst to obtain the corresponding polymers with moderate molecular weights ($\overline M _{\rm n}$ = 8 400 to 32 000) in 45 to 86% yields. Polarimetric, circular dichroism (CD), and UV‐vis spectroscopic analyses revealed that poly(1) and poly(6) took a helical structure with, predominantly, a one‐handed screw sense. On the other hand, poly[(S)HCCCH~2~OCOCH(CH~3~)OH] [poly(1′)], an ester analogue of poly(1), and poly(2)–poly(5) did not take a predominantly one‐handed helical structure.

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