Dialkylamido Sulfoxylic Acid Fluorides, I: Synthesis and Reactions with Olefins

Abstract

The reaction of potassium fluoride with the corresponding acid chlorides results in the formation of dialkylamido sulfoxylic acid fluorides Alk ₂ N-S-F. Stereo- and regioselectivity of dimethylamido and diisopropylamido sulfoxylic acid fluorides addition reactions to the C,C double bond in cyclohexene, 3,4-dihydro-2H-pyrane, and vinyl ethyl ether has been investigated. This reaction is a convenient approach to the β -fluoroalkyl sulfenic acid derivatives.

Keywords:

• Alkenes
• fluorides of dialkylamido sulfoxylic acids
• fluorinating reagents
• β-fluoroalkyl sulfenic acid

Dedicated to Professor Marian Mikołajczyk, CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

Notes

^a Conformations with the NMe₂ group oriented towards the ring possess higher energies and are not considered here.

^b Bold marked values are referred to the most favored conformations for the cis- and trans-isomers.