Development of a novel geminal-difluorination method and its application in the synthesis of sup 18 F-labeled fatty acid analogues as potential myocardial imaging agents
An efficient two-step fluorination procedure for transforming a ketone or aldehyde to the corresponding gem-difluoro compound has been developed. The gem-difluoro compounds can be prepared by first forming the corresponding 1,3-dithiolane followed by reaction with 1,3-dibromo-5,5-dimethylhydantoin and pyridinium poly(hydrogen fluoride). The reaction requires 2 equivalents of Br{sup +} and appears to proceed through a sequence of two bromosulfonium ions that open and cleave, respectively, to sulfur- and fluorine-stabilized carbocations that are trapped by fluoride ion. A convenient, general synthetic route to functionalized fatty acids has been developed and utilized in the synthesis of (16-{sup 18}F),6,6-trifluorohexadecanoic acid and (16-{sup 18}F)7,7-trifluorohexadecanoic acid as potential myocardial imaging agents. Corey's 2-lithio-1,3-dithiane methodology was employed both to link two terminally difunctionalized carbon chains, thereby producing the fatty acid precursor, and to introduce the 1,3-dithiane which would ultimately become a gem-difluoromethylene group.
- Research Organization:
- Illinois Univ., Urbana, IL (USA)
- OSTI ID:
- 7245572
- Resource Relation:
- Other Information: Thesis (Ph. D.)
- Country of Publication:
- United States
- Language:
- English
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MYOCARDIUM
IMAGE PROCESSING
RADIOPHARMACEUTICALS
CHEMICAL PREPARATION
CARBOXYLIC ACIDS
FLUORINE 18
PRECURSOR
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BODY
CARDIOVASCULAR SYSTEM
DRUGS
FLUORINE ISOTOPES
HEART
HOURS LIVING RADIOISOTOPES
ISOMERIC TRANSITION ISOTOPES
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
MUSCLES
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
PROCESSING
RADIOISOTOPES
SYNTHESIS
550601* - Medicine- Unsealed Radionuclides in Diagnostics