Electrophilic additions of positive iodine to alkynes through an iodonium mechanism
Тип публикации: Journal Article
Дата публикации: 1990-05-01
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Краткое описание
Alkynes react with bis(pyridine)iodonium(I) tetrafluoroborate(1) and nucleophiles (CH 3 COOH, HCOOH, Cl − , pyridine, Br − , I − ) to give 1,2-iodofunctionalized alkenes. The regiochemistry of the processes is in accordance with the polar effects of the triple bond substituents. With regard to stereochemistry, terminal alkynes yield anti addition products, but internal ones produce anti addition with weaker nucleophiles (CH 3 COOH, HCOOH, Cl − , pyridine), syn with stronger nucleophiles (I − ), and a mixture of anti and syn with borderline nucleophiles (Br − ) or when the internal alkyne bears a bulky group. An ionic mechanism through a vinyleneiodonium ion is proposed to explain the obtained results
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ГОСТ
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Barluenga J., Rodriguez M. A., Campos P. J. Electrophilic additions of positive iodine to alkynes through an iodonium mechanism // Journal of Organic Chemistry. 1990. Vol. 55. No. 10. pp. 3104-3106.
ГОСТ со всеми авторами (до 50)
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Barluenga J., Rodriguez M. A., Campos P. J. Electrophilic additions of positive iodine to alkynes through an iodonium mechanism // Journal of Organic Chemistry. 1990. Vol. 55. No. 10. pp. 3104-3106.
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TY - JOUR
DO - 10.1021/jo00297a027
UR - https://doi.org/10.1021/jo00297a027
TI - Electrophilic additions of positive iodine to alkynes through an iodonium mechanism
T2 - Journal of Organic Chemistry
AU - Barluenga, José
AU - Rodriguez, M A
AU - Campos, Pedro J
PY - 1990
DA - 1990/05/01
PB - American Chemical Society (ACS)
SP - 3104-3106
IS - 10
VL - 55
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (до 50 авторов)
Скопировать
@article{1990_Barluenga,
author = {José Barluenga and M A Rodriguez and Pedro J Campos},
title = {Electrophilic additions of positive iodine to alkynes through an iodonium mechanism},
journal = {Journal of Organic Chemistry},
year = {1990},
volume = {55},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jo00297a027},
number = {10},
pages = {3104--3106},
doi = {10.1021/jo00297a027}
}
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MLA
Скопировать
Barluenga, José, et al. “Electrophilic additions of positive iodine to alkynes through an iodonium mechanism.” Journal of Organic Chemistry, vol. 55, no. 10, May. 1990, pp. 3104-3106. https://doi.org/10.1021/jo00297a027.