N-Pentyl nitrite

N,N-Dimethylaniline n-Pentyl nitrite Phenyl chlorothionoformate 4-Dimethylaminopyridine Tri-n-butyltin hydride... 

Example 107 The reaction of Example 86 was repeated, except that 3-(4-methoxy-3-methylphenyl) propylene, n-pentyl nitrite, and n-pentyl alcohol were used in lieu of 3-(4-hydroxyphenyl) propylene, methyl nitrite, and methyl alcohol and that the reaction temperature was 60° C. and the hydrolysis was carried out at 50° C. for 60 minutes. 

Dideoxynebularine (2 ,3 -dideoxypurine nucleoside, ddPN) 1 was one of a number of C-6 modified purine dideoxynucleosides synthesized in our laboratory (Scheme 2). It was designed to be a prodrug of ddl and was synthesized from 5 -protected ddA by reductive deamination using a procedure previously developed by us, followed by deprotection. Compound 1 was found to be inactive against the cytopathic effect of HIV-l and HIV-2 in MT-4 cells. It was not toxic to MT-4 cells at 200 jiM. It was not a substrate for xanthine oxidase. In contrast, C-6 substituted purine dideoxynucleosides that are substrates for mammalian ADA, show anti-HIV activity [e.g., 6-iodo ddPN, 2, synthesized from 5 -protected ddA by radical deamination/halogenation (n-pentyl nitrite, CH,L, CHjCN, A), followed by deprotection]. 

The rate coefficient values available for 2-butyl nitrite, 2-methyl-l-propyl nitrite, 2-methyl-2-propyl nitrite, and 1-pentyl nitrite are given in table VIII-I-12. As mentioned for other alkyl nitrites, the measurements of Audley et al. (1982) might be overestimated. The rate coefficient determinations for the reaction of OH with n-pentyl nitrite of Nielsen et al. (1991) using both relative and absolute methods are in reasonable agreement. 

The sole study of a higher alkyl nitrite, n-pentyl nitrite, is that of Nielsen et al. (1991). A relative rate method was used at ambient temperature and atmospheric pressure. The rate coefficient value obtained is given in table Vni-I-13. However, as described in the reaction of Cl with CH3ONO, the Nielsen et al. (1991) measurement could have been... 

Table VIII-l-13. Rate coefficient (k, cm molecule s ) for the reaction of Cl with n-pentyl nitrite (n-CsHnONO)...

Methylpyridazine can be oxidized with selenium dioxide to give 3-formylpyridazine, and methyl groups attached to any position in pyridazine N-oxides are transformed with pentyl nitrite in the presence of sodium amide in liquid ammonia into the corresponding... 

Pentyl amine, see n-Amylamine Iso-Pentyl nitrite, see Amyl nitrite Peracetic acid (40% acetic acid solution)... 

N-Methylmorphollne 1-Nitropef>tane Pentyl nitrite tsopentyl nitrite Pentyl nitrate... 

Pentanone, see Methyl n-propyl ketone 3- Pentanone, see Diethyl ketone Pentene, see Amylene n-Pentyl acetate, see n-Amyl acetate sec-Pentyl acetate, see sec-Amyl acetate Pentyl alcohol, see n-Amyl alcohol Pentyl amine, see n-Amylamine iso-Pentyl nitrite, see Amyl nitrite Peracetic acid (40% acetic acid 1.23 41... 

Aromatic annotation." The reaction of dibenzoyl peroxide (1 mole) with a large excess ofdimethyl acetylenedicarboxylate( 10 mole)at 80° gives tetramethyl naphthalene-1,2,3,4-tetracarboxylate (0.5 mole/mole peroxide). The reaction proceeds through a phenyl radical, since other sources of phenyl radicals (N-nitrosoacetanilide or acetanilide-pentyl nitrite) can replace the dibenzoyl peroxide. The reaction is believed to proceed by addition of the phenyl radical to the acetylene followed by further addition... 

Polyhydric phenols can also be doubly nitrosated. Heinrich289 obtained 4-nitrosoresorcinol as potassium salt on dropping pentyl nitrite into a cooled solution of resorcinol and potassium hydroxide in absolute alcohol, but resorcinol is easily doubly nitrosated, at the 2,4-positions, by nitrous acid in an acid solution.289 290 N.B. preparation of trinitrosophloroglucinol may lead to an explosion.291... 

The reaction of pentafluoroaniline with pentyl nitrite at about 80 °C provides a good source of the pentafluorophenyl radical (probably via CgFg NrN OPe — CJ ,- -h N -I- PeO-) (c/. pa 395). 2,3,4,5,6-Ptenta-fluorobiphenyl is formed in 58% yield when this reaction is carried out in... 

If Ar = HiCO, a good yield of benzoyl cyanide is obtained. Allylic triphenyl-phosphonium halides react similarly with pentyl (isoamyl) nitrite and the products are decomposed by ethanolic potassium hydroxide to nitriles, for example, -methylcinnamonitrile is obtained in 57% yield and famesyl cyanide in 87% yield [127J. N-Nitroso compounds give nitriles on reaction with triphenylphos-phine alkylenes [128], for example... 

---