202-03-9Relevant articles and documents
Application of flash vacuum pyrolysis to the synthesis of sulfur- containing heteroaromatic systems
Imamura, Koichi,Hirayama, Daigo,Yoshimura, Hitoshi,Takimiya, Kazuo,Yoshio, Aso,Otsubo, Tetsuo
, p. 2789 - 2792 (2007/10/03)
The FVP method of ethynyl and chlorovinyl materials is applied to the ready formation of sulfur-containing fused heteroaromatic systems. The pyrolysis of the chlorovinyl materials is assumed to involve a mechanism different from that of the ethynyl materials.
The Pyrolysis of Phenylnaphthalene-dicarboxylic Anhydrides: Products of Ring Contraction and of Radical Cyclization
Anderson, Mark R.,Brown, Roger F. C.,Coulston, Karen J.,Eastwood, Frank W.,Ward, Annemarie
, p. 1137 - 1150 (2007/10/02)
Naphthalene-1,2-dicarboxylic anhydrides with neighbouring phenyl substituents give on flash vacuum pyrolysis (850-900 deg C/ 0.02-0.04 mm) ring-contracted carbenes which insert into the phenyl groups.The 8-phenyl anhydride (7) gives acephenanthrylene (10) as the major product, and the 3-phenyl anhydride (15) gives 1,2:4,5-dibenzopentalene (indenoindene) (18).The anhydides (7) and (15) were synthesized by pyrolisis of the corresponding 1-naphthylmethyl propynoates (2) and (13) through a new one-step process of intramolecular Diels-Alder addition/retro-Diels-Alder elimination of acetylene. 1-Phenylnaphthalene-2,3-dicarboxylic anhydride (19) on pyrolysis at 960 deg C/0.02 mm gives fluoranthene (11) as the major product.The behaviour of the 1-C6D5 compound (24) suggests involvement of radical cyclization process.
