Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1 '-cyclopropane] derivatives

BAYRAK, Cetin; ŞENOL, Halil; SIRTBAŞI, Sedef; Şahin, Ertan; MENZEK, Abdullah

doi:10.1016/j.tet.2018.07.060

Makale Tam Makale Uluslararası 2018

Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1 '-cyclopropane] derivatives

Cetin BAYRAK, Halil ŞENOL, Sedef SIRTBAŞI, Ertan Şahin, Abdullah MENZEK

TETRAHEDRON Cilt 74 · Sayı 40 · ss. 5839–5849 · 04.10.2018

DOI ile aç

Özet

Reactions of benzyne with ester derivatives of spiro[2.4]hepta-4,6-dien-1-ylmethanol were performed. By rearrangement reaction of cyclopropyl methanol units of ((1s*,1'R*,2R*,4'S*)-1',4'-dihydrospiro [cyclopropane-1,9'-[1,4]methanonaphthalen]-2-yl) methyl 3,5-dinitrobenzoate (13) and its isomer (14), corresponding allyl chlorides were obtained. Two rearrangement products were obtained from bromination of compound 13 with an equivalent amount of Br-2. A naphthalene derivative including allyl and CHO moiety was formed for reactions from compounds with epoxide of 13 and 14 with NaN3 by sequential rearrangements. Formations of products are discussed. (C) 2018 Elsevier Ltd. All rights reserved.

Anahtar kelimeler

SYSTEM STABILITY GENERATION benzonorbornadiene HIGH-TEMPERATURE BROMINATION Alkenes Rearrangement CYCLOADDITION REACTION Cycloaddition Bromination Spirocyclopentadiene Epoxide Cyclopropylmethanol BENZHOMOBARRELENE DERIVATIVES BENZYNE BONDS

Atıf için künye

BAYRAK, C., ŞENOL, H., SIRTBAŞI, S., Şahin, E., & MENZEK, A. (2018). Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1 '-cyclopropane] derivatives. TETRAHEDRON, 74(40), 5839–5849. https://doi.org/10.1016/j.tet.2018.07.060

BibTeX

@article{bayrak2018-66812,
  author = {BAYRAK, Cetin and ŞENOL, Halil and SIRTBAŞI, Sedef and Şahin, Ertan and MENZEK, Abdullah},
  title = {Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1 '-cyclopropane] derivatives},
  journal = {TETRAHEDRON},
  year = {2018},
  volume = {74},
  number = {40},
  pages = {5839--5849},
  issn = {0040-4020},
  doi = {10.1016/j.tet.2018.07.060},
  url = {https://akademik.atauni.edu.tr/yayinlar/66812-synthesis-and-rearrangement-reactions-of-14-dihydrospiro14-methanonaphthalene-91}
}