Synthesis and Structural Determination of Two Types of Novel Cyclic Carbonates

Abstract

Two types of novel cyclic carbonates, including 7-benzylidene-4,6-oxa-5- carbonyl–spiro[2,4] heptane 3a and 7-phenyl-4,6-oxa-5-carbonyl–spiro [2,5] 7-octene 4a, were readily synthesized from 1-alkynyl cyclopropyl ^tButyl carbonate by using AuCl(PPh₃)/ Ag(OTf) as catalysts. The structure of compound 3a was identified to be a 5-member cyclic carbonate by X-ray crystallographic analysis, of which the unit cell has monoclinic P2(1)/c symmetry with the cell parameters a = 7.0543(14) Å, b = 10.556(2) Å, c = 13.066(3) Å, and Z = 4. Therefore, the structure of compound 4a can be deduced to be a six membered cyclopropane-containing cyclic carbonate.

Keywords:

• 1-alkynyl cycloproanol
• AuCl(PPh₃) catalyst
• cyclic carbonates
• spiro compounds

Support of this work by a starter grant from Renmin University of China and the grant from National Sciences Foundation of China (No.20502033) are gratefully acknowledged.