Benzyl-isopropyl

Secondary and tertiary alkyl halides are not suitable because they react with alkox ide bases by E2 elimination rather than by 8 2 substitution Whether the alkoxide base IS primary secondary or tertiary is much less important than the nature of the alkyl halide Thus benzyl isopropyl ether is prepared m high yield from benzyl chloride a pri mary chloride that is incapable of undergoing elimination and sodium isopropoxide... 

Since there is inherent in reactions which give low selectivities, the possibility that non-competitive conditions are responsible, Olah and Overchuck359 have measured directly the rates of benzylation, isopropylation, and fer/.-butylation of benzene and toluene with aluminium and stannic chlorides in nitromethane at 25 °C. Apparent second-order rate coefficients were obtained (assuming that the concentration of catalyst remains constant), but it must be admitted that the kinetic plots showed considerable departure from second-order behaviour. The observed rate coefficients and kreh values determined by the competition method are given in Table 88, which seems to clearly indicate that the competitive ex-... 

Reductive Thiolation. Treatment of aldehydes with triethylsilane, thiols, and boron trifluoride monohydrate 217 yields sulfides in a one-flask process. For example, this method gives a 97% yield of benzyl isopropyl sulfide from benzaldehyde and 2-propanethiol (Eq. 204).365... 

Bis-[ 1-ethyl-propyloxy]- XII/2, 291 Bis-[2-ethylthio-ethoxyJ- XII/2, 27 Bis-fferrocenylmethoxy]- El, 331 Bis-[2-fluor-ethoxy]- XII/2, 24 Bis-[l-hydroxy-benzyl]-isopropyl- XII/1, 157 Bis-f2-hydroxy-ethoxy]- XII/2, 21 Bis-[2-hydroxy-ethyl]-hydroxymethyl- E2, 54 Bis-[hydroxymethyl]-cyclohexyl- E2. 53 Bis-[hydroxymethyl]-isopropyl- E2, 53 Bis-[hydroxymethyl]-methyl- XII/1, 142 E2, 48,... 

The woik of Tuleen and Stevens on the regioselectivity of chlorination of a series of unsymmetrically substituted dialkyl sulfides with NCS provides clues to Ae directive effects implicit in the mechanisms encompassed by Scheme 3. These observations are collected in Scheme 6 where the preferred site of chlorination in each case is indicated with an arrow, the number over the arrow indicating the majortminor product ratio (minor = 1). In the first example, chlorination of benzyl methyl sulfide (2) produces chlorobenzyl methyl sulfide exclusively. Secondly, chlorination of benzyl ethyl sulfide (3) and benzyl isopropyl sulfide (4) also shows a marked, though not exclusive, preference for the benzylic position. In the latter case the extent of benzylic chlorination can be modulated by ring substitution. The directive effects in these internal competitions for p-methyl and p-chloro substituents are correlated by the Hammett relationship with a value of p = 1.0, which is consistent with a mechanism involving abstraction of the more acidic proton in the chlorosulfonium ion intermediate. Further indications of the im-... 

Benzyl-isopropyl- IV/ld, 350, 358 Butyl-phenyl- XI/1, 224, 634, 947 Diethyl-phenyl- XI/1,136f 206, 216,... 

Keten Benzyl-isopropyl- E15/2, 2367 (R2CH — CO — Cl/Amin) Naphthalin... 

A combination of trimethylsilyl bromide and zinc triflate promoted the glycosylation of benzyl-, isopropyl-, and methyl glycosides with several glycosyl acceptors in moderate to good yields [241,242],... 

Thus benzyl isopropyl ether is prepared in high yield from benzyl chloride, a primary chloride that is incapable of undergoing elimination, and sodium isopropoxide ... 

Photolysis of DTBP in solution containing benzyl isopropyl ether/ Benzene... 

Propyl p-tolyl sulphoxides, Z7.6 Mesityl methyl sulphoxide, Z8.5 Benzyl isopropyl sulphoxide, Z 5.6 C10H14O2... 

Figure 2 Synthesis of cyclol moiety of natural ergopeptines R]=methyl, ethyl or isopropyl R2=benzyl, isopropyl, isohutyl or sec-butyl...

Acetophenone Propiophenone Benzyl isopropyl ketone Butyrophenone... 

Percentage Reduced to Carbinol 35.7, as phenyl methyl carbinol 26, as phenyl ethyl carbinol 43, as benzyl isopropyl carbinol 41, as phenyl n-propyl carbinol... 

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