Synthesis Of Oxygen-17 Labeled Alcohols Via Organoborane Reactions

George Kabalka, Tim J. Reed, Sastry A. Kunda

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Oxygen-17 enriched alcohols play an increasingly important role in chemical, biological, and medical research1. Traditionally these reagents are prepared via hydrolysis of a suitable acetal or ketal with oxygen-17 labeled water followed by reduction of the oxygen labeled carbonyl compounds2. This sequence produces good yields of volatile, unsubstituted alcohols but is of limited use in the preparation of materials containing reducible or hydrolyzable functional groups. Organoboranes have proven to be extremely versatile synthetic reagents3,4. In recent years, we have utilized organoborane chemistry to incorporate isotopes of carbon5, iodine6, bromine7, and nitrogen8. We now wish to report that oxygen-17 labeled, functionally substituted alcohols can be readily synthesized via the direct reaction of17O-labeled oxygen gas with organoboranes.

Original languageEnglish (US)
Pages (from-to)737-740
Number of pages4
JournalSynthetic Communications
Volume13
Issue number9
DOIs
StatePublished - Jul 1 1983
Externally publishedYes

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Alcohols
Oxygen
Acetals
Isotopes
Functional groups
Hydrolysis
Gases
Water

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Synthesis Of Oxygen-17 Labeled Alcohols Via Organoborane Reactions. / Kabalka, George; Reed, Tim J.; Kunda, Sastry A.

In: Synthetic Communications, Vol. 13, No. 9, 01.07.1983, p. 737-740.

Research output: Contribution to journalArticle

Kabalka, George ; Reed, Tim J. ; Kunda, Sastry A. / Synthesis Of Oxygen-17 Labeled Alcohols Via Organoborane Reactions. In: Synthetic Communications. 1983 ; Vol. 13, No. 9. pp. 737-740.
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