Alcoholysis of fluoroform

Fedor M. Miloserdov; Vladimir V. Grushin

doi:10.1016/j.jfluchem.2014.06.006

Alcoholysis of fluoroform

Fedor M. Miloserdov, Vladimir V. Grushin^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

8 Citations (Scopus)

Abstract

Fluoroform (CHF₃) reacts with alkali metal alkoxides MOR (M = Na, K) in the corresponding alcohols ROH (R = Me, Et, i-Pr, t-Bu, and Allyl) at 80-120°C to give orthoformate esters HC(OR)₃ in 55-90% yield. Particularly notable is the formation of HC(OBu-t)₃ in 75-80% yield (62% isolated yield; X-ray), an exotic organic compound that has been previously synthesized only once (3% yield). Solutions of NaOH in ROH (R = Me, Et, i-Pr and t-Bu) react with CHF₃ to give NaF, HCOONa, and orthoformates HC(OR)₃. Hydrolysis of fluoroform with MOH (M = Na, K) at 140°C produces largely MF and HCOOM along with small quantities of CO.

Original language	English
Pages (from-to)	105-109
Number of pages	5
Journal	Journal of Fluorine Chemistry
Volume	167
DOIs	https://doi.org/10.1016/j.jfluchem.2014.06.006
Publication status	Published - Nov 2014
Externally published	Yes

Keywords

Alcoholysis
CHF
Fluoroform
HFC-23
Orthoformates

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10.1016/j.jfluchem.2014.06.006

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@article{b09c4e0e032548dcb6fdfe2d881ebf7f,

title = "Alcoholysis of fluoroform",

abstract = "Fluoroform (CHF3) reacts with alkali metal alkoxides MOR (M = Na, K) in the corresponding alcohols ROH (R = Me, Et, i-Pr, t-Bu, and Allyl) at 80-120°C to give orthoformate esters HC(OR)3 in 55-90% yield. Particularly notable is the formation of HC(OBu-t)3 in 75-80% yield (62% isolated yield; X-ray), an exotic organic compound that has been previously synthesized only once (3% yield). Solutions of NaOH in ROH (R = Me, Et, i-Pr and t-Bu) react with CHF3 to give NaF, HCOONa, and orthoformates HC(OR)3. Hydrolysis of fluoroform with MOH (M = Na, K) at 140°C produces largely MF and HCOOM along with small quantities of CO.",

keywords = "Alcoholysis, CHF, Fluoroform, HFC-23, Orthoformates",

author = "Miloserdov, {Fedor M.} and Grushin, {Vladimir V.}",

year = "2014",

month = nov,

doi = "10.1016/j.jfluchem.2014.06.006",

language = "English",

volume = "167",

pages = "105--109",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier",

}

TY - JOUR

T1 - Alcoholysis of fluoroform

AU - Miloserdov, Fedor M.

AU - Grushin, Vladimir V.

PY - 2014/11

Y1 - 2014/11

N2 - Fluoroform (CHF3) reacts with alkali metal alkoxides MOR (M = Na, K) in the corresponding alcohols ROH (R = Me, Et, i-Pr, t-Bu, and Allyl) at 80-120°C to give orthoformate esters HC(OR)3 in 55-90% yield. Particularly notable is the formation of HC(OBu-t)3 in 75-80% yield (62% isolated yield; X-ray), an exotic organic compound that has been previously synthesized only once (3% yield). Solutions of NaOH in ROH (R = Me, Et, i-Pr and t-Bu) react with CHF3 to give NaF, HCOONa, and orthoformates HC(OR)3. Hydrolysis of fluoroform with MOH (M = Na, K) at 140°C produces largely MF and HCOOM along with small quantities of CO.

AB - Fluoroform (CHF3) reacts with alkali metal alkoxides MOR (M = Na, K) in the corresponding alcohols ROH (R = Me, Et, i-Pr, t-Bu, and Allyl) at 80-120°C to give orthoformate esters HC(OR)3 in 55-90% yield. Particularly notable is the formation of HC(OBu-t)3 in 75-80% yield (62% isolated yield; X-ray), an exotic organic compound that has been previously synthesized only once (3% yield). Solutions of NaOH in ROH (R = Me, Et, i-Pr and t-Bu) react with CHF3 to give NaF, HCOONa, and orthoformates HC(OR)3. Hydrolysis of fluoroform with MOH (M = Na, K) at 140°C produces largely MF and HCOOM along with small quantities of CO.

KW - Alcoholysis

KW - CHF

KW - Fluoroform

KW - HFC-23

KW - Orthoformates

U2 - 10.1016/j.jfluchem.2014.06.006

DO - 10.1016/j.jfluchem.2014.06.006

M3 - Article

AN - SCOPUS:85027955723

SN - 0022-1139

VL - 167

SP - 105

EP - 109

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

Alcoholysis of fluoroform

Abstract

Keywords

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