Synthesis of hexabromo, hydroxy, epoxy, methoxy and nitroxy derivatives of tetralins and naphthalenes

Abstract

Stereoselective synthesises are described for naphthalene and tetralin derivatives. Hexabromo 2 and 3, monomethoxy 7, dimethoxy 6, dihydroxy 4 and dinitroxy 10 derivatives of tetralin have been obtained. Base-promoted elimination reactions of 6 and 4 provided monomethoxy 8 and 9 and diepoxy 5 naphthalenes respectively. The structures of these products were determined by 1 H and 13 C NMR spectra, mass spectra and micro analysis.

<b>SYNTHESIS OF ALLENIC NAPHTHALENE DERIVATIVES</b>

“…In previous work, we described hydroxyl, epoxyl, methoxyl and nitroxyl derivatives of naphthalene [7]. The present work reports the synthesis of allenic derivatives of naphthalene.…”

“…1-(Naphthlen-5-yl)-3-phenylprop-2-yn-1-ol 3d (0.90 g, 3.48 mmol), Ac 2 O (2 mL), pyridine (3 drops 7.28-7.46 (m, 4H), 7.46-7.59 (m, 5H), 7.89 (m, 3 H), 8.30 (d, J = 8.5 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ), δ: 21.1, 64.5, 85.6, 87.5, 122.1, 123.8, 125.2, 125.9, 126.5, 126.6, 128.2, 128.7, 128.8, 129.9, 130.6, 131.9, 132.4, 134.0, 169.9 3, 97.6, 123.7, 125.8, 125.9, 126.4, 127.1, 127.4, 128.1, 128.8, 128.9, 129.9, 131.0, 133.9, 134.1, 209 13 C NMR (100 MHz, CDCl 3 ), δ: 23. 8, 83.7, 87.3, 123.5, 123.8, 125.7, 125.8, 126.3, 127.7, 127.9, 128.3 (2C), 128.8, 131.6, 131.8, 132.6, 133.9 1-(Propa-1,2-dienyl)naphthalene (7). To a solution of trimethyl (3-(naphthalene-5-yl)prop-1-ynyl)silane (0.178 g, 0.75 mmol) in THF (5.0 mL) was added C 2 H 5 ONa (61.2 mg, 0.9 mmol) in THF (3.0 mL) under argon at rt.…”

2,4-Dibromo-2,3-dihydro-1H-inden-1-yl acetate

“…For bromination of hydrocarbons, see : Catto et al (2010); Erenler & Ç akmak (2004); Erenler et al (2006); McClure et al (2011); Mitrochkine et al (1995); Snyder & Brill (2011);Wu (2006);Ç akmak et al (2006). For puckering parameters, see: Cremer & Pople (1975 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009 Brominations of hydrocarbons are important processes in synthetic chemistry (Çakmak et al, 2006;Erenler et al, 2006;Erenler & Çakmak, 2004).…”

Synthesis, Crystal and Molecular Structure of 2′,3′,3′-Tribromo-2′,3′-dihydrospiro[1,3-dioxolane-2,1′-indene]

“…Brominations of hydrocarbons are important processes in synthetic chemistry [6][7][8][9][10]. The materials obtained from bromination of hydrocarbons have numerous industrial applications as pesticides, plastics, fire retardants and pharmaceutical chemicals [11].…”