Wydział Chemii

Nurbey Gulia

Jolanta Ejfler

Sławomir Szafert

2012

Tetrahedron Letters

53

5471-5474

10.1016/j.tetlet.2012.07.141

Naukowa

Angielski

Artykuł

A Mannich condensation of 2,4-di-tert-butylphenol, p-bromophenethylamine, and formaldehyde followed by a Sonogashira coupling of the resulting 3-(4-bromophenethyl)-6,8-di-tert-butyl-3,4-dihydro-2H-benz[1,3]oxazine (1-Br) with TMSCCH gave acetylenic benzoxazine 1-C₂TMS which was a precursor for polyynic derivatives. Firstly, it was deprotected with K₂CO₃ in iPrOH/MeOH to give the terminal acetylene 1-C₂H, which was subsequently dimerized to the symmetrical diyne 1-C₄-1. Next, 1-C₂H was transformed to 1-C₄TMS via a Cadiot–Chodkiewicz coupling, and then 1-C₄TMS was homocoupled with in situ deprotection to give octatetrayne 1-C₈-1. X-ray diffraction studies of 1-C₈-1 showed distinctive chain bending and a packing analysis revealed the potential for 1,n-topochemical polymerization that implies a cross-linking opportunity.

Polyynes

https://doi.org/10.1016/j.tetlet.2012.07.141

http://www.elsevier.com