Mild and high-yielding syntheses of diethyl phosphoramidate-stoppered [2]rotaxanes

Wei-Chung Hung; Kang-Shyang Liao; Yi-Hung Liu; Shie-Ming Peng; Sheng-Hsien Chiu

doi:10.1021/ol0484557

Mild and high-yielding syntheses of diethyl phosphoramidate-stoppered [2]rotaxanes

Org Lett. 2004 Nov 11;6(23):4183-6. doi: 10.1021/ol0484557.

Authors

Wei-Chung Hung¹, Kang-Shyang Liao, Yi-Hung Liu, Shie-Ming Peng, Sheng-Hsien Chiu

Affiliation

¹ Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, Taiwan 10617, R.O.C.

PMID: 15524438
DOI: 10.1021/ol0484557

Abstract

The mild and efficient reaction between triethyl phosphite and benzylic azides allows us not only to construct rotaxanes in high yield from dibenzo[24]crown-8 (DB24C8) and dibenzylammonium (DBA(+))-derived threads but also to incorporate di(p-toluidine)[24]crown-8, which binds DBA(+) ions much more weakly than does DB24C8, into a corresponding [2]rotaxane.