Benzyl alcohol 2-butene

Methyl n-amyl carbinol. 247, 254 Methyl n-amyl ketone, 482 Methylaniline (mono), pure, from commercial methylaniline, 562, 570 P-Methylanthraquinone, 728, 740 Methyl benzoate, 780, 781 p-Methyl benzyl alcohol, 811,812 Methyl benzyl ketone, 727, 735 Methyl y-bromocrotonate, 926, 927 2-Methyl-2-butene, 239 Methyl n-butyl carbinol, 247,255 Methyl n-butyl ether, 314 Methyl n-butyl ketone, 475, 481 4-Methylcarbostyril, 855 p-Methylcinnamic acid, 719 4-Methylcoumarin, 853, 854 Methyl crotonate, 926, 927 Methylethylacetic acid, 354, 358 Methylethylethynyl carbinol, 468 Methyl ethyl ketone, 335, 336 purification of, 172 Methyl n-hexyl ether, 314 Methyl n-hexyl ketone, 335, 336 Methyl n-hexyl ketoxime, 348 Methyl hydrogen adipate, 938 Methyl hydrogen sebacate, 938,939 4-Methyl-7-hydroxycoumarin, 834 Methyl iodide, 287 Methyl isopropyl carbinol, 247,255 Methyl 4-keto-octanoate, 936... 

Doyle and co-workers have employed Rh2(pfb)4 as a highly selective catalyst for the room temperature synthesis of silyl ethers from alcohols and triethylsilane.159 The selectivity of the catalyst is demonstrated by reactions of olefinic alcohols, in which hydrosilylation is not competitive with silane alcoholysis when equimolar amounts of silane and alcohol are employed. High yields (>85%) of triethylsilyl ethers are obtained from reactions of alcohols such as benzyl alcohol, 1-octanol, 3-buten-l-ol, cholesterol, and phenol. Tertiary alcohols are not active in this system. 

Intramolecular reaction with nucleophilic groups can also lead to heterocycles. For example, good yields of 3-acylbenzofurans result from cyclization caused by intramolecular substitution of the tertiary amino group by a phenol formed by cleavage of a phenol ether by boron tribromide251 (equation 182). 0-Hydroxy benzyl alcohols were used to obtain 4//-chromenes by their reaction with 4-morpholino-3-buten-2-one in acetic acid-acetic anhydride187. 

Similarly, chromium-complexed benzylic cations are also stabilized and organic reactions based on the benzylic cation species have been developed. For example, planar chiral o-substituted benzaldehyde dimethylacetal chromium complexes 4 were treated with 3-buten-l-ol in the presence of TiCl4 to give tet-rahydropyran derivatives with high diastereoselectivity (Eq. 5) [5]. The chromium-complexed benzylic oxonium ion 6 would be also generated and subsequent intramolecular cyclization afforded the cyclization product 7. Furthermore, the chromium-complexed benzyl alcohol derivative having electron-rich arene ring at the side chain produced tetrahydroisoquinoline skeleton by treatment with Lewis acid with stereochemical retention at the benzylic position (Eq. 6) [6]. 

Room temperature trifluoroethanol, trichloroethanol, phenols, chloral hydrate, formic acid, chloro-acetic acid, HF, HCl, methanol, H2SO4, phosphoric add, benzyl alcohol, ethylene chlorohydrin, 1,3 chloropropanol, 2-butene-l,4,diol., diethylene glycol, acetic acid, formamide, DMSO... 

The first example of the ruthenium-catalyzed synthesis of amides from alcohols and amines was reported by Murahashi et al. in 1991 [82aj. The contrast results were obtained from the RuH2(PPh3)4-catalyzed reaction of 5-aminopentanol. Thus, piperidine was obtained in 79% yield, while similar treatment in the presence of a hydrogen acceptor of l-phenyl-l-buten-3-one gave piperidone in 65% yield (Eq. (7.36)). Recently, Williams reported the intermolecular amidation reaction of benzyl alcohols with amines in the presence of [Ru(p-cymene)Cl2]2 and 3-methyl-2-butanone [82bj. 

Alkylation of 7V-benzyl-p-toluenesulfonamide (12a) with a threefold excess of fra j-l,4-dichloro-2-butene (ila) gives the allylic chloride 11b. which is treated with sodium acetate in DMF followed by hydrolysis to afford the allylic alcohol 10a in an overall 68% yield. 

Hamill, Guarino, and Ronayne (II) gamma irradiated 0.18 mole % benzyl chloride in glassy 2-methyltetrahydrofuran (MTHF) at liquid nitrogen temperature and obtained a maximum ultraviolet absorption band at 320 m/x in agreement with Porter and Strachan, see Table I. They also irradiated 1.0 mole % allyl chloride, allyl bromide and allyl alcohol in 3-methylpentane (3-MP) and in all cases observed a maximum absorption band at 228 m/x which they attributed to the allyl free radical. They also irradiated 3-chloro-1-butene and 3-chlorocyclohexene in 3-MP and determined the wavelengths of the absorption band maxima of the 1-methyl allyl and 2-cyclohexen-l-yl free radicals given in Table I. 

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