An efficient protocol for synthesizing dibenzodithiapentalenes

TY - JOUR

T1 - An efficient protocol for synthesizing dibenzodithiapentalenes

AU - Jepsen, Tue Heesgaard

AU - Larsen, Mogens

AU - Jørgensen, Morten

AU - Nielsen, Mogens Brøndsted

PY - 2011/8/3

Y1 - 2011/8/3

N2 - Two new scalable methods for the synthesis of dibenzo[bc,fg]dithiapentalene (2) (DPP) are reported starting from either 1-bromo-3-fluoro-2-iodobenzene over four steps in 57% yield or from THP-protected 3-fluorothiophenol over three steps in 43% yield. Attempts to prepare dibenzodioxapentalene (15) using similar conditions were unsuccessful. Instead, we observed the formation of a macrocyclic dimeric product 16. Fluorine-hydrogen bond interactions were observed by NMR in the F/SH- and F/OH-substituted dibenzothiophene and dibenzofuran intermediates.

AB - Two new scalable methods for the synthesis of dibenzo[bc,fg]dithiapentalene (2) (DPP) are reported starting from either 1-bromo-3-fluoro-2-iodobenzene over four steps in 57% yield or from THP-protected 3-fluorothiophenol over three steps in 43% yield. Attempts to prepare dibenzodioxapentalene (15) using similar conditions were unsuccessful. Instead, we observed the formation of a macrocyclic dimeric product 16. Fluorine-hydrogen bond interactions were observed by NMR in the F/SH- and F/OH-substituted dibenzothiophene and dibenzofuran intermediates.

M3 - Journal article

SN - 0040-4039

VL - 52

SP - 4045

EP - 4047

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -