Synthesis of N-confused porphyrin analogues by β-azafulvenone tetramerization

GGH Qiao, MW Wong, C Wentrup

Index: Qiao, Greg GuangHua; Wong, Ming Wah; Wentrup, Curt Journal of Organic Chemistry, 1996 , vol. 61, # 23 p. 8125 - 8131

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Citation Number: 12

Abstract

Flash vacuum thermolysis (FVT) of the same α-oxo diazo ketone 14 at 650 °C gave the same ketene, isolated in Ar matrix at 12 K. ... 2. Tetramerization of 16 to 1,3'-tetrakis(indolylmethanone ) (20). Isolation of ketene 16 at 12 K and subsequent warmup revealed that this ketene is only stable below 58 K. This instability is due to the imine function which acts as a nucleophile toward another ketene molecule. 18 IR spectroscopy showed that the product of this thermal ...