A text-book of practical organic chemistry, including by Arthur Israel Vogel

By Arthur Israel Vogel

The most effective books there's instructing functional natural chemistry. The 3rd version of this publication (first released in 1956) is basically of far better use to the pastime chemist, because it doesn't utilize any hideously dear glassware/apparatus or unique reagents or catalysts.

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88,369 (1966). C. J. Collins and W. A. Bonner, J. Am. Chem. , 77,6725 (1955). 61 J. W. Wilt, J. F. Zawadzki, and D. G. Sohultenover, J . Org. , 31,876 (1966). 59 60 Organic Reaction Mechanisms 1966 24 (100) Participation by Double and Triple Bonds Reviews of the formation of cyclopropane and cyclobutane rings through participation by double bondss2and on transannular participations3have been published. It was originally reportedB4 that the acetolysis of exo-norbornen-2-yl p-bromobenzenesulphonate (101) labelled with 14C a t C(21 and C(3) yielded acetate in which the label was scrambled, but not as much as required by the intervention of the symmetrical ion (102).

Ll0~ll1The fact that the acetolysis of 1-methylcyclopropyl toluenep-sulphonate proceeds only 150 times faster than that of cyclopropyl toluenep-sulphonate a t 150" suggests that the ring-opening is concerted with ionisation and that the reactions do not involve the free cyclopropyl cation. The effect of 2,3-dirnethyl substituents on the rate depends on whether they are cis or trans to the leaving toluene-p-sulphonyloxy-group (see Table 7). This difference was interpreted in terms of Woodward and Hoffmann's prediction'lz that the preferred modes of ring opening are the disrotatory ones (165) and Pierre and P.

77 30 Orgariic Reaction Mechaiiisnzs 1966 symbolized by (129)and (130), does not occur in the acetolyses of synnorbornen-7-ylmethyl p-bromobenzenesulphonate (see also p. *~ The rates and products of solvolysis of a series of homoallylic halides and have been arenesulphonates of general structure R,CH=CH-CH,-CH,-X determined. 79 Other investigations of participation by double bonds include studies of ion-pair return in the perchloric acid isomerization of isochloesteryl acetate (see p. s5a M. Hanack, S.

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