A stabilized and persistent tetraketene: 1,4-bis(1′,4′-dioxo-3′-trimethylsilyl-2′-buta-1′,3′-dienyl)benzene

doi:10.1139/V95-224

Paper

A stabilized and persistent tetraketene: 1,4-bis(1′,4′-dioxo-3′-trimethylsilyl-2′-buta-1′,3′-dienyl)benzene

Published Nov 1, 1995 · Ronghua Liu, T. Tidwell

Canadian Journal of Chemistry

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Abstract

Reaction of 1,4-bis(trimethylsilylethynyl)benzene with CCl3COCl and Zn gave 1,4-bis(4′,4′-dichloro-2′-trimethylsilyl-3′-oxo-1′-cyclobutenyl)benzene (7), which reacted with concentrated H2SO4 at 87 °C to give 1,4-bis(2′-trimethylsilyl-3′,4′-dioxo-1′-cyclobutenyl)benzene (8). Photolysis of 8 in CDCl3 with 350 nm light gave the bisketene 9, which on further photolysis formed the title tetraketene 10, as identified by its spectral properties. Upon heating of 10 the successive closure of the two bisketene moieties, first to give the mono(cyclobutenedione) 9 and then to reform 8 in a slower step, was observed by NMR and UV spectroscopy. Reaction of 10 with MeOH gave the tetraester 11, which was assigned the erythro configuration at each of the succinate moieties. Keywords: ketenes, photolysis, cyclobutenediones, esterification, silicon.

Study Snapshot

This study presents a stable and persistent tetraketene, 1,4-bis(1′,4′-dioxo-3′-trimethylsilyl-2′-buta-1′,3′-dienyl)benzene, which can be converted into cyclobutened

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

A stabilized and persistent tetraketene: 1,4-bis(1′,4′-dioxo-3′-trimethylsilyl-2′-buta-1′,3′-dienyl)benzene

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