Diethyl azodicarboxyl ate

One of these reagents, Ph3P, triphenylphosphine, is a simple phosphine, rather like an amine but with P instead of N. The other deserves more comment. Its full name is diethyl azodicarboxyl ate, or DEAD. 

Diethyl azodicarboxyl ate is purchased from Aldrich Chemical Company, Inc., and is used without further purification. 

INVERSION, LACTONES Triphenyl-phosphine-Diethyl azodicarboxyl-ate. 

Mitsunobu reaction has also found use for the synthesis of nucleoside analogues. The reactions of diphosphines with cyanamide or sulphamide in the presence of diethyl azodicarboxyl ate have given bis-azenes, e.g.,(76). In a similar manner tris-X -azenes have been obtained from triphosphines Bis(diphenyl-phosphino)methane reacts cleanly with trimethylsilylazide to give, initially, one isomeric form of the silylated monophosphazene (77)... 

Cyclization of 1 -amino-8-(2-hydroxyalkyl)-4-oxoquinoline-3-carboxyl-ates (130) on the action of diethyl azodicarboxylate in the presence of triphenylphosphine afforded 7-oxopyrido[3,2,l-jy]cinnoline-8-carboxylates (131) (92EUP470578). 

Direct alkylation of hydrazine itself with halides and sulfates usually gives mixtures of mono- and poly-alkylated hydrazines. It is possible to get useful yields of the monoalkylhydrazine by using an excess of hydrazine. Several specific procedures leading to monoalkylhydrazines are based on selective alkylation of hydrazine derivatives with protecting groups attached. So, easily prepared acetone N-(diethoxyphosphoryl)hydrazone (75) can be used. Phase-transfer catalyzed N-alkylation of (75), followed by deprotection with p-toluenesulfonic acid provides monoalkylhydrazine sulfonates (76 Scheme 17). Similarly, N-alkyl-N-arylhydrazines have been prepared by phase-transfer catalyzed N-alkylation of arylhydrazones (Scheme 18). An efficient, one-pot method for the synthesis of a variety of polysilyl-ated hydrazines employs hexamethyldisilane (equation 30). Polysilylated hydrazines were found to react with aldehydes or ketones to give hydrazones under anhydrous conditions. By treatment with triphenylphosphine and diethyl azodicarboxylate primary and secondary alcohols can be converted to hy-dr ine derivatives (equation 31). ... 

Additions to compounds with activated double or triple bonds are known. Compound 406 (R = Me) gives 427 with acrylonitrile(405 does not react ), and 401 reacts with diethyl azodicarboxylate and maleic anhydride to give 428 and 429, respectively. The 2,6-dimethyl derivative of 396 undergoes addition to dimethyl acetylenedicarboxyl-ate at C-5 (position a. Scheme 18), but tetracyanoethylene gives both C-5 and C-7 (a and b) products, the latter predominating. Reid had earlier reported that 396 reacts with bulky electrophiles to give mixtures of products and disubstituted derivatives. 

Diethyl Azodi carboxyl ate Triphenylphosphine-Diethyl Azodicarboxylate C6H12O... 

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