DEHYDROBENZENE IN THE REACTION OF A TANDEM [4+2]/[4+2] CYCLOADDITION WITH LINEAR BIS-FURYLDIENES

Authors

  • Elizaveta A. Kvyatkovskaya Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Polina P. Epifanova Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Kseniya K. Borisova Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Sophia I. Borovkova Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Mikhail S. Grigoriev A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31, Build. 4 Leninsky Ave., Moscow 119071, Russia
  • Fedor I. Zubkov Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia

DOI:

https://doi.org/10.1007/6364

Keywords:

aryne, dehydrobenzene, 1, 4, 5, 8-diepoxynaphthalenes, furan, 7-oxabicyclo[2.2.1]heptane, IMDAF reaction, intramolecular Diels–Alder reaction, tandem [4 2]/[4 2] cycloaddition.

Abstract

Tandem [4+2]/[4+2] cycloaddition between bis-dienes containing two furan rings and dehydrobenzene as a dienophile was studied. It was shown that dehydrobenzene generated in situ from 2-(trimethylsilyl)phenyl trifluoromethanesulfonate is capable of a facile intermolecular [4+2] cycloaddition to a furan moiety of a diene at room temperature. The next step, that involves intramolecular Diels–Alder reaction (the IMDAF reaction) with the second furan ring, requires elevated temperature up to 80°С. It has been shown that even under optimal conditions the yields of the target annulated 1,4:5,8-diepoxynaphthalenes do not exceed 50%. The main byproducts are double cycloaddition adducts formed during the interaction of two aryne subunits with both furan rings of the initial bis-diene.

Author Biography

Elizaveta A. Kvyatkovskaya, Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia

Organic Chemistry Department, Faculty of Science, RUDN University, Russia

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Published

2021-09-22

Issue

Vol. 57 No. 9 (2021)

Section

Original Papers