Reaction of 9-oxabicyclo[4.2.1]non-7-ene-1-ol with tetrazine: An unusually facile intramolecular rearrangement

KAYA, Adem; Salamcı, Emine; MENZEK, Abdullah; ERDEM, SAFİYE; Şahin, Ertan; ECER, Kadriye

doi:10.1016/j.tet.2017.07.040

Makale Tam Makale Uluslararası 2017

Reaction of 9-oxabicyclo[4.2.1]non-7-ene-1-ol with tetrazine: An unusually facile intramolecular rearrangement

Adem KAYA, Emine Salamcı, Abdullah MENZEK, SAFİYE ERDEM, Ertan Şahin, Kadriye ECER

TETRAHEDRON Cilt 73 · Sayı 36 · ss. 5381–5388 · 07.09.2017

DOI ile aç

Özet

Reaction of (1S(*), 7R(*))-9-oxabicyclo[4.2.1]non-7-en-1 -ol (5) with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (6) produced (2R(*),4R(*))-dimethyl 4-(7-oxooxepan-2-yl)-1,4-dihydropyridazine-3,6-dicarboxylate (11) in a one-pot reaction involving cycloaddition at ambient conditions. The structure of the rearrangement product 11 was determined by X-ray crystallographic analysis. Its formation was discussed based on experimental studies and density functional theory calculations. The driving force of this unusually facile reaction was the stability of the caprolactone product 11 and the extremely exorgenic loss of N-2. Structural factors facilitating this rearrangement were also explored employing PCM//M06-2X/6-31G(d, p) calculations. (C)2017 Elsevier Ltd. All rights reserved.

Anahtar kelimeler

CONVERSION CHEMISTRY DERIVATIVES 1 MECHANISM DFT Diels Alder Caprolactone 4-Epoxide Rearrangement Retro-ene Tetrazine BICYCLIC ENDOPEROXIDES SYNTHETIC APPLICATIONS CYCLOADDITION REACTION ENE REACTION DOUBLE-BOND THERMOLYSIS

Atıf için künye

KAYA, A., Salamcı, E., MENZEK, A., ERDEM, S., Şahin, E., & ECER, K. (2017). Reaction of 9-oxabicyclo[4.2.1]non-7-ene-1-ol with tetrazine: An unusually facile intramolecular rearrangement. TETRAHEDRON, 73(36), 5381–5388. https://doi.org/10.1016/j.tet.2017.07.040

BibTeX

@article{kaya2017-66548,
  author = {KAYA, Adem and Salamcı, Emine and MENZEK, Abdullah and ERDEM, SAFİYE and Şahin, Ertan and ECER, Kadriye},
  title = {Reaction of 9-oxabicyclo[4.2.1]non-7-ene-1-ol with tetrazine: An unusually facile intramolecular rearrangement},
  journal = {TETRAHEDRON},
  year = {2017},
  volume = {73},
  number = {36},
  pages = {5381--5388},
  issn = {0040-4020},
  doi = {10.1016/j.tet.2017.07.040},
  url = {https://akademik.atauni.edu.tr/yayinlar/66548-reaction-of-9-oxabicyclo421non-7-ene-1-ol-with-tetrazine-an-unusually-facile}
}