Preparation of chlorofluoroacetic acid derivatives for the analysis of chiral 
alcohols

Streinz, Ludvik; Svatoš, Aleš; Vrkoč, Jan; Meinwald, Jerrold

doi:10.1039/p19940003509

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

Preparation of chlorofluoroacetic acid derivatives for the analysis of chiral alcohols

MPS-Authors

There are no MPG-Authors in the publication available

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

Streinz, L., Svatoš, A., Vrkoč, J., & Meinwald, J. (1994). Preparation of chlorofluoroacetic acid derivatives for the analysis of chiral alcohols. Journal of the Chemical Society, Perkin Transactions 1, (23), 3509-3512. doi:10.1039/p19940003509.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0015-0E2B-E

Abstract

(R)- and (S)- Chlorofluoroacetic acid (CFA) esters of several chiral secondary alcohols have been prepared and compared with the corresponding esters of Mosher's acid. CFA itself is a readily accessible and optically stable acid which gives the expected diastereoisomeric products with chiral alcohols without epimerization. The resulting diastereoisomers are more volatile than those derived from Mosher's acid, and are well resolved by both GC and HPLC. Both H-1 and F-19 NMR spectra of CFA esters show characteristic signals in regions rarely overlapped by other signals. Since CFA is a strong organic acid, it reacts with alcohols spontaneously to give esters without any additional catalysis.