The Journal of Organic Chemistry

Effects of temperature on atom transfer cyclization reactions of allylic. alpha.-iodo esters and amides

DP Curran, J Tamine

Index: Curran, Dennis P.; Tamine, John Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2746 - 2750

Full Text: HTML

Citation Number: 196

Abstract

Atom-transfer cyclizations of allyl iodoacetatee and N-allyl-N-methyliodoacetamides are much more efficient at 80" C than at 25" C. At 80" C, & (iodomethyl) lactones and lactams are formed rapidly and in good yield under standard atom-transfer conditions (sunlamp irradiation of iodide and 10% hexabutylditin in benzene for 10-60 min). It is proposed that this temperature effect is responsible for some unusual observations by Jolly and ...

Related Articles:

A tandem aza-Claisen rearrangement and ring closing metathesis reaction for the synthesis of cyclic allylic trichloroacetamides

[Swift, Michael D.; Sutherland, Andrew Organic Letters, 2007 , vol. 9, # 25 p. 5239 - 5242]

Complementary Reactions of Allylic Carbamates Using Palladium (II): Formation of Oxazolidinones or Allylic Amides from a Common Precursor

[Christie, Steven D. R.; Warrington, Adam D.; Lunniss, Christopher J. Synthesis, 2009 , # 1 p. 148 - 154]

Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium–arene complexes

[Borguet, Yannick; Sauvage, Xavier; Zaragoza, Guillermo; Demonceau, Albert; Delaude, Lionel Beilstein Journal of Organic Chemistry, 2010 , vol. 6, p. 1167 - 1173]

Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium–arene complexes

[Borguet, Yannick; Sauvage, Xavier; Zaragoza, Guillermo; Demonceau, Albert; Delaude, Lionel Beilstein Journal of Organic Chemistry, 2010 , vol. 6, p. 1167 - 1173]

Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium–arene complexes

[Borguet, Yannick; Sauvage, Xavier; Zaragoza, Guillermo; Demonceau, Albert; Delaude, Lionel Beilstein Journal of Organic Chemistry, 2010 , vol. 6, p. 1167 - 1173]

More Articles...