Single electron transfer mechanism in the reaction of 1, 3-dithianyllithium and alkyl iodides

E Juaristi, HA Jimenez-Vazquez

Index: Juaristi, Eusebio; Jimenez-Vazquez, Hugo A. Journal of Organic Chemistry, 1991 , vol. 56, # 4 p. 1623 - 1630

Full Text: HTML

Citation Number: 35

Abstract

The reaction between 2-lithio-l, 3-dithiane and optically active (R)-2-iodooctane was found to proceed with complete inversion of configuration. This result suggests that the SN2 (rather than single electron transfer (SET)) mechanism is the preferred pathway for reaction between dithianyllithium and unhindered alkyl halides. When the neopentyl-type radical probe 5, 5-dimethyl-6-iodo-l-hexene was used as the substrate halide, 6-1 1% cyclized ...

Related Articles:

Ultrasound-accelerated synthesis of chiral allylic alcohols promoted by indium metal

[Yadav; Reddy; Srinivasa Reddy Tetrahedron, 2003 , vol. 59, # 28 p. 5333 - 5336]

Titanium tetrachloride promoted reactions of allylic trimethylsilanes and oxetane

[Carr, Steve A.; Weber, William P. Journal of Organic Chemistry, 1985 , vol. 50, # 15 p. 2782 - 2785]

Selective dehydration of alkanediols into unsaturated alcohols over rare earth oxide catalysts

[Yamanaka, Tohr; Imai, Takashi Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 5 p. 1585 - 1586]

Facile Synthesis of Spirocyclic Systems through the Intramolecular Addition of Ketyl Radicals via the Sodium/Ammonia Reduction of δ, ε-Unsaturated Carboxylic …

[Journal of Organic Chemistry, , vol. 63, # 9 p. 3141 - 3146]

Alkyl Radical Generation in Water under Ambient Conditions—A New Look at the Guareschi Reaction of 1897

[Angewandte Chemie - International Edition, , vol. 46, # 40 p. 7655 - 7658]

More Articles...