A Convenient Synthesis of 1,6-Dioxapyrene-2,7-dicarboxylic Acid Diethyl Ester.

A new donor for charge-transfer systems: synthesis and properties of 2,4,7,9-tetramethyl-1,6-dithiapyrene (TMDTP) and structure of (TMDTP)3(PF6)2·2THF and TMDTP–TCNQ

“…30,31 This led to the question if it would be possible to use the pyrene p-frame as a test tube for investigating the effect of the heteroatom on the conducting materials properties. Since it is not possible to synthesize 1,6-dioxapyrenes by the same methodology 32 (Scheme 1), different methodologies have been developed based either on 2,6-dialkyl-1,5-naphthalenediols as starting materials 33,34 or on using 1,4,5,8-tetrasubstituted naphthalenes as intermediates [35][36][37][38] but both strategies have their limitations.…”

4,8-Bisallyl-2,6-dimethylnaphthalene-1,5-diyl Diacetate

“…We [4][5][6][7] and other groups [8][9][10][11] have previously reported different methodologies for the synthesis of 1,6-dioxa-and 1,6-dithiapyrenes from naphthalene derivatives and while the 1,6-dithiapyrenes can be synthesized from 1,5-disubstituted naphthalenes through an acid catalyzed ring closure, the synthesis of 1,6-dioxapyrenes requires either 1,2,5,6-tetrasubstituted naphthalenes or 1,4,5,8-tetrasubstituted napthalenes as intermediates.…”

Rhodium-Catalyzed Cascade Oxidative Annulation Leading to Substituted Naphtho[1,8-bc]pyrans by Sequential Cleavage of C(sp2)–H/C(sp3)–H and C(sp2)–H/O–H Bonds

“…Substituted naphtho­[1,8- bc ]­pyran moieties are an important structural unit present in various naturally occurring and synthetic compounds that exhibit a broad range of interesting biological and optoelectronic properties . However, only a few synthetic routes are reported in the literature, and most of them require a complicated multistep process or inaccessible starting materials. − Recently, groups of Satoh and Miura, and Ackermann respectively reported rhodium- and ruthenium-catalyzed naphtho­[1,8- bc ]­pyran synthesis from a 1-naphthol substrate via hydroxyl-directed C–H bond activation (eq 2). However, very limited substituted 1-naphthol substrates were examined in their work.…”