Fluorinated Building Blocks. The Discovery of a Stable Difluoroallenyl Indium and the Synthesis of gem-Difluoroallenyl and -propargyl Synthons in Aqueous Media
Publication type: Journal Article
Publication date: 2000-09-13
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
11052100
Organic Chemistry
Abstract
The synthesis of two highly functional fluorinated motifs, TIPS-C triple bond C-CF2-, and CF2=C=C(TIPS)- is described. This approach is mediated by a room-temperature stable ethereal solution of a difluoroallene indium intermediate. This intermediate may be used as "stock solution" in the reaction with aqueous HCHO, to yield CF2=C=C(TIPS)CH2OH, and in a reaction with a Schiff base to produce the corresponding beta,beta-difluorohomopropargylamine. The synthetic potential of CF2=C=C(TIPS)CH2-OH has been demonstrated by its conversion to a difluorodihydrofuran derivative by a facile and efficient 5-endo-trig cyclization. Homopropargylic gem-difluoro alcohols are synthesized by addition of indium to a mixture of an aldehyde and TIPS-C triple bond C-CF2Br in predominantly aqueous media.
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GOST
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Wang Z., HAMMOND G. B. Fluorinated Building Blocks. The Discovery of a Stable Difluoroallenyl Indium and the Synthesis of gem-Difluoroallenyl and -propargyl Synthons in Aqueous Media // Journal of Organic Chemistry. 2000. Vol. 65. No. 20. pp. 6547-6552.
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Wang Z., HAMMOND G. B. Fluorinated Building Blocks. The Discovery of a Stable Difluoroallenyl Indium and the Synthesis of gem-Difluoroallenyl and -propargyl Synthons in Aqueous Media // Journal of Organic Chemistry. 2000. Vol. 65. No. 20. pp. 6547-6552.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo000832f
UR - https://doi.org/10.1021/jo000832f
TI - Fluorinated Building Blocks. The Discovery of a Stable Difluoroallenyl Indium and the Synthesis of gem-Difluoroallenyl and -propargyl Synthons in Aqueous Media
T2 - Journal of Organic Chemistry
AU - Wang, Zhigang
AU - HAMMOND, Gerald B.
PY - 2000
DA - 2000/09/13
PB - American Chemical Society (ACS)
SP - 6547-6552
IS - 20
VL - 65
PMID - 11052100
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2000_Wang,
author = {Zhigang Wang and Gerald B. HAMMOND},
title = {Fluorinated Building Blocks. The Discovery of a Stable Difluoroallenyl Indium and the Synthesis of gem-Difluoroallenyl and -propargyl Synthons in Aqueous Media},
journal = {Journal of Organic Chemistry},
year = {2000},
volume = {65},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/jo000832f},
number = {20},
pages = {6547--6552},
doi = {10.1021/jo000832f}
}
Cite this
MLA
Copy
Wang, Zhigang, and Gerald B. HAMMOND. “Fluorinated Building Blocks. The Discovery of a Stable Difluoroallenyl Indium and the Synthesis of gem-Difluoroallenyl and -propargyl Synthons in Aqueous Media.” Journal of Organic Chemistry, vol. 65, no. 20, Sep. 2000, pp. 6547-6552. https://doi.org/10.1021/jo000832f.