scholarly journals Iron-mediated intermolecular N-group transfer chemistry with olefinic substrates

2014 ◽  
Vol 5 (4) ◽  
pp. 1526-1532 ◽  
Author(s):  
Elisabeth T. Hennessy ◽  
Richard Y. Liu ◽  
Diana A. Iovan ◽  
Ryan A. Duncan ◽  
Theodore A. Betley
Keyword(s):  
High Spin ◽  
Transfer Reaction ◽  
Group Transfer

We present a chemoselective group transfer reaction from a high-spin ferric imido to olefinic and benzylic substrates.

Correlation of the solid-state reactivities of racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate and its 4,4′-bipyridine cocrystal with their crystal structures

2014 ◽  
Vol 70 (11) ◽  
pp. 1040-1045 ◽  
Author(s):  
Majid I. Tamboli ◽  
Vir Bahadur ◽  
Rajesh G. Gonnade ◽  
Mysore S. Shashidhar
Keyword(s):  
Solid State ◽  
Self Assembly ◽  
Transfer Reaction ◽  
Acyl Transfer ◽  
Transfer Reactions ◽  
Group Transfer ◽  
Hydrogen Bonding Interactions ◽  
Benzoyl Group ◽  
The Stability ◽  
Group Migration

Racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate, C21H18O8,(1), shows a very efficient intermolecular benzoyl-group migration reaction in its crystals. However, the presence of 4,4′-bipyridine molecules in its cocrystal, C21H18O8·C10H8N2,(1)·BP, inhibits the intermolecular benzoyl-group transfer reaction. In(1), molecules are assembled around the crystallographic twofold screw axis (baxis) to form a helical self-assembly through conventional O—H...O hydrogen-bonding interactions. This helical association places the reactive C6-O-benzoyl group (electrophile, El) and the C4-hydroxy group (nucleophile, Nu) in proximity, with a preorganized El...Nu geometry favourable for the acyl transfer reaction. In the cocrystal(1)·BP, the dibenzoate and bipyridine molecules are arranged alternately through O—H...N interactions. The presence of the bipyridine molecules perturbs the regular helical assembly of the dibenzoate molecules and thus restricts the solid-state reactivity. Hence, unlike the parent dibenzoate crystals, the cocrystals do not exhibit benzoyl-transfer reactions. This approach is useful for increasing the stability of small molecules in the crystalline state and could find application in the design of functional solids.

Dual-Face Nucleoside Scaffold Featuring a Stereogenic All-Carbon Quaternary Center. Intramolecular Silicon Tethered Group-Transfer Reaction

2014 ◽  
Vol 16 (21) ◽  
pp. 5698-5701 ◽  
Author(s):  
Guillaume Tambutet ◽  
Fabiola Becerril-Jiménez ◽  
Starr Dostie ◽  
Ryan Simard ◽  
Michel Prévost ◽  
...  
Keyword(s):  
Transfer Reaction ◽  
Group Transfer ◽  
Quaternary Center

Synthese und Photolyse von 5-Diazo-5-[13C] -homoadamantanon-(4).

1976 ◽  
Vol 31 (5) ◽  
pp. 586-588 ◽  
Author(s):  
Klaus-Peter Zeller
Keyword(s):  
Carboxylic Acid ◽  
Transfer Reaction ◽  
Uv Light ◽  
Intermediate Formation ◽  
Ring Expansion ◽  
Group Transfer ◽  
Total Absence ◽  
Adamantane Skeleton ◽  
Diazo Group

The synthesis of 5-diazo-5-[13C]-homoadamantan-4-one (12) is achieved by ring expansion of adamantanone with 13C-labelled diazomethane, conversion of the resulting 4-[13C]-homoadamantan-4-one (10) to the hydroxymethylene compound (11), followed by deformylative diazo group transfer reaction. The photolysis of 12 with pyrex filtered UV-light in dioxane-water (10:1) yields adamantan-2-carboxylic acid containing all the label in the 2-position of the adamantane skeleton. The total absence of isotope scrambling excludes the intermediate formation of the polycyclic oxiren (16) (Scheme 3).

Polymergebundenes Sulfonylazid zur entformylierenden Diazogruppen-Übertragung und zur Diazo -cyclopolyen -Synthese / Polymer Anchored Sulfonylazide for Deformylating Diazo Group Transfer and the Synthesis of Diazo-cyclopolyenes

1981 ◽  
Vol 36 (9) ◽  
pp. 1149-1152 ◽  
Author(s):  
Heinz Dürr ◽  
Gerhard Hauck ◽  
Wolfgang Brück ◽  
Helge Kober
Keyword(s):  
Low Temperature ◽  
Transfer Reaction ◽  
Diazo Compound ◽  
Alternative Route ◽  
Secondary Product ◽  
Group Transfer ◽  
Sulfonyl Azide ◽  
Polymer Anchored ◽  
Cyclic Polyenes ◽  
Diazo Group

AbstractPolymer anchored sulfonylazide is compared with its efficiency in the diazogroup transfer reaction of tosylazide. The resulting yields with the polymeric reaction are slightly lower than with tosylazide. However the greater thermostability of polymeric sulfonyl azide and its workup procedure make this alternative very attractive for synthesis. The reaction of polymeric sulfonyl azide with cyclic polyenes gives very small yields compared with the monomeric reaction. The attempt to generate diazocyclononatetraene by an alternative route leads only to the secondary product namely indene. At low temperature, and intermediate diazo-compound is, however, observed, which is tentatively assigned to structure 12.

Synthesis of C6F5-Substituted Aminoethanols via Acetate Ion Mediated C6F5-Group Transfer Reaction

Synthesis ◽  
2006 ◽  
pp. 489-495 ◽  
Author(s):  
Alexander D. Dilman ◽  
Vitalij V. Levin ◽  
Pavel A. Belyakov ◽  
Alexander A. Korlyukov ◽  
Marina I. Struchkova ◽  
...  
Keyword(s):  
Transfer Reaction ◽  
Group Transfer
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