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Communication | Special issue | Vol 11, No. 1, 1978, pp.299-304
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0299
10-Mesity-9-arsaanthracene

Ruud J. M. Weustink, Pieter J. A. Geurink, and Friedrich Bickelhaupt*

*Scheikundig Laboratorium, Vrije Universiteit, De Boelelaan, 1083 NL-1081 HV Amsterdam, The Netherlands

Abstract

The highly sterically hindered, 10-mesityl-9-arsaanthracene (1c) has been prepared by pyrolysis of the dihydro-precursor (3). Due to steric hindrance at the 10-position, 1c is the most stable of all known derivatives of arsaanthracane; even the Diels-Alder reaction with maleic anhydride is slow and reversible at ambient temperatures, leading to the 9,10-adduct 4. At higher temperatures, an alternative Diels-Alder reaction yields the 1,4-adduct 5, the first known derivative of arsanaphthalene. The carbon analog 6 of 1c gives the corrasponding 1,4-adduct 7.