Dihaloadamantanes: Ring Closure versus Rearrangement or Halogen-Displacement Reactions
Publication type: Journal Article
Publication date: 2004-07-01
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Three dihaloadamantanes [i.e., 2-bromo-1-(chloromethyl)adamantane (1), 1-(bromomethyl)-2-chloroadamantane (2) and 2-bromo-1-(bromomethyl)adamantane (3)] were synthesized, and their corresponding ring-closing reactions, performed by using Na metal or alkyllithium reagents, were studied. Compound 1 reacted with Na in toluene or in tetraglyme to afford 1,2-methanoadamantane (4) as the major product. However, the corresponding reactions, when performed by using 2 and 3 as substrates, produced methyladamantane (5) or 4-methyleneprotoadamantane (6) as the major reaction products. The corresponding reactions of 1 and 2 with tBuLi or nBuLi afforded small quantities of 4, 5 and 6 along with the corresponding monohalides, that is, 1-(chloromethyl)adamantane (7) and 2-chloro-1-methyladamantane (8), which constituted the major products of these reactions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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Total citations:
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Citations from 2024:
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(11.11%)
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Mlinarić-Majerski K. et al. Dihaloadamantanes: Ring Closure versus Rearrangement or Halogen-Displacement Reactions // European Journal of Organic Chemistry. 2004. Vol. 2004. No. 13. pp. 2923-2927.
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Mlinarić-Majerski K., Veljković J., Kaselj M., Marchand A. P. Dihaloadamantanes: Ring Closure versus Rearrangement or Halogen-Displacement Reactions // European Journal of Organic Chemistry. 2004. Vol. 2004. No. 13. pp. 2923-2927.
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TY - JOUR
DO - 10.1002/ejoc.200400121
UR - https://doi.org/10.1002/ejoc.200400121
TI - Dihaloadamantanes: Ring Closure versus Rearrangement or Halogen-Displacement Reactions
T2 - European Journal of Organic Chemistry
AU - Mlinarić-Majerski, Kata
AU - Veljković, Jelena
AU - Kaselj, Mira
AU - Marchand, Alan P.
PY - 2004
DA - 2004/07/01
PB - Wiley
SP - 2923-2927
IS - 13
VL - 2004
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2004_Mlinarić-Majerski,
author = {Kata Mlinarić-Majerski and Jelena Veljković and Mira Kaselj and Alan P. Marchand},
title = {Dihaloadamantanes: Ring Closure versus Rearrangement or Halogen-Displacement Reactions},
journal = {European Journal of Organic Chemistry},
year = {2004},
volume = {2004},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/ejoc.200400121},
number = {13},
pages = {2923--2927},
doi = {10.1002/ejoc.200400121}
}
Cite this
MLA
Copy
Mlinarić-Majerski, Kata, et al. “Dihaloadamantanes: Ring Closure versus Rearrangement or Halogen-Displacement Reactions.” European Journal of Organic Chemistry, vol. 2004, no. 13, Jul. 2004, pp. 2923-2927. https://doi.org/10.1002/ejoc.200400121.