Showing papers by "Harold W. Moore published in 2001"
15 Apr 2001
TL;DR: In this article, the authors used 2,5-diazido-3,6-di-tert-butyl-1,4-benzoquinone to synthesize tertbutylcyanoketene, a versatile ketene for reactions with a variety of ketenophiles.
Abstract: [29342-21-0] C14H18N6O2 (MW 302.38)
InChI = 1S/C14H18N6O2/c1-13(2,3)7-9(17-19-15)12(22)8(14(4,5)6)10(11(7)21)18-20-16/h1-6H3
InChIKey = IKPZTVQMWPXVCY-UHFFFAOYSA-N
(reagent for the preparation of tert-butylcyanoketene,2 a versatile ketene for reactions with a variety of ketenophiles1)
Physical Data: mp 89–90 °C (dec).
Solubility: sol aromatic solvents which are used in the preparation of tert-butylcyanoketene.
Analysis of Reagent Purity: IR (Nujol) 2110 (N3), 1640 (CO) cm−1; 1H NMR (CDCl3), δ 1.31 (s, tert-Bu).
Preparative Method: 2,5-diazido-3,6-di-tert-butyl-1,4-benzoquinone 2 is readily synthesized in five steps from commercially available 2,5-di-tert-butyl-1,4-benzoquinone 1 in approximately 30% overall yield (eqs 1-3).2
(1)
(2)
(3)
Purification: recrystallization from chloroform/ethanol.
Handling, Storage, and Precautions: during the course of any purification method that might be employed, the diazide should not be heated above 50 °C since decomposition occurs quite noticeably at that temperature. It is best to store the pure product below −5 °C in the dark since it undergoes a facile photochemical rearrangement to a cyclopentenedione.2