Premium
Preparation of a Key Tetraene Precursor for the Synthesis of Long Acenes
Author(s) -
Levet Gaspard,
Hung Nguyen Khanh,
Šámal Michal,
Rybáček Jiří,
Cisařová Ivana,
Jancarik Andrej,
Gourdon André
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901868
Subject(s) - chemistry , ozonolysis , maleic anhydride , fulvene , carboxylation , double bond , yield (engineering) , organic chemistry , medicinal chemistry , catalysis , materials science , copolymer , metallurgy , polymer
The tetraene 7,7‐dimethoxy‐2,3,5,6‐tetramethylenebicyclo[2.2.1]heptane is a key compound for the preparation of a large variety of acenes protected by a carbonyl bridge. We report herein a medium scale preparation in seven steps of this valuable starting material. Diels–Alder addition between 6,6‐dimethtyl fulvene and maleic anhydride, followed by carboxylation, ozonolysis of the double bond, reduction of the four ester groups, then chlorination of the alcohol groups and dehydrochlorination give the target compound in 17 % overall yield.