The reaction of N-methyl-1,2,4-triazoline-3,5-dione with tetracyclopropylethylene. Formation of an unusual meso-ionic product and its rearrangement to the diazetidine

Duk Kyung Kim; Kevin E O'Shea

doi:10.1021/ja038359l

The reaction of N-methyl-1,2,4-triazoline-3,5-dione with tetracyclopropylethylene. Formation of an unusual meso-ionic product and its rearrangement to the diazetidine

J Am Chem Soc. 2004 Jan 28;126(3):700-1. doi: 10.1021/ja038359l.

Authors

Duk Kyung Kim¹, Kevin E O'Shea

Affiliation

¹ Department of Chemistry, Florida International University, University Park, Miami, Florida 33199, USA.

PMID: 14733528
DOI: 10.1021/ja038359l

Abstract

The reaction of N-methyl-1,2,4-triazoline-3,5-dione and tetracyclopropylethylene results in the quantitative formation of a meso-ionic compound. The formation of this unusual compound is likely the result of the unique conformational and steric properties of the cyclopropyl groups which inhibit the expected reaction pathways. The meso-ionic compound undergoes an unprecedented rearrangement to the diazetidine upon warming to 55 degrees C.