An unprecedented rearrangement of a 1,1-diprotected hydrazine derivative. Structure revision of a catalyst-containing by-product

作者：Ragnarsson Ulf^*; Grehn Leif; Pehk Tonis

来源：Tetrahedron Letters, 2014, 55(51): 7019-7022.

DOI：10.1016/j.tetlet.2014.10.121

• Hydrazine derivative
• Nucleophilic catalysis
• Rearrangement
• Structure revision
• Tetramethylguanidine

Treatment of 1-Boc-1-tosyl-hydrazine with 1,1,3,3-tetramethylguanidine (TMG) gave rise to two products, one containing and the other not containing TMG. The latter was identified as 1-Boc-2-tosyl-hydrazine. This rearrangement provided useful insight into the nature of the first product that had previously been isolated and assigned an incorrect tentative structure. To rationalize the results a plausible mechanism via a common intermediate, involving TMG as a nucleophilic catalyst is proposed. A simpler procedure for the preparation of the starting material is also presented.

• 出版日期2014-12-17