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polymer reagent (peracid) and low-molecular-weight substrate (alkene), often with a solvent for the latter, are allowed to react and then ltered. Solvent is evaporated from the ltrate to yield the low-molecular-weight product (epoxide); puri cation steps such as distillation may also be involved. From the economic viewpoint, it is desirable if the polymer reagent can be regenerated from the polymer by-product (polymer acid). This is easily accomplished in the particular example as the polymer acid yields the peracid on treatment with hydrogen peroxide. It is not possible to obtain the economy of polymer regeneration in all polymer reagent systems. Polymer peracids have also been used for the oxidation of sul des to sulfoxides and sulfones [Grieg et al., 1980; Harrison and Hodge, 1976]. Oxidation of alcohols to aldehydes or ketones is accomplished with chromate bound to an anion-exhange resin (XXXIX with A HCrO ) [Frechet et al., 1981; Taylor, 1986]. Other 4 oxidants include polymers functionalized with ClO , ClCrO , and RuO [Kirschning et al., 4 4 2001]:

Polymer reducing agents for reducing aldehydes and ketones to alcohols are obtained by complexing AlH3 or BH3 with a nitrogen-containing polymer such as poly(4-vinylpyridine) (e.g., XXXX) [Boga et al, 1989; Menger et al., 1980]. Another useful reducing reagent is XXXIX with A BH , which involves ionic bonding of boron hydride anion to a quater4 nary ammonium polymer [Sande et al., 1984]. The use of a chiral polymer instead of the achiral polymers in XXXIX and XXXX allows an asymmetric synthesis. An example is the stereoselective reduction of acetophenone to (R)-1-phenylethanol in 76 97% enantiomeric excess by using the indicated chiral support (Eq. 9-69) [Itsuno et al., 1985]:

THE UNITED STATES IN THE TWENTIETH CENTURY: 1946 1990

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Parts . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 245 Open It Up! . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 245

9-69

Pyridinium bromide, useful for bromine addition to alkenes and a-substitution on aldehydes and ketones, is dangerous to handle. The polymer analog (XXXXI) is easy to handle

seasoned issues, and 1981 peak yields were more than six times greater than 1946 low yields The great bear market lasted some thirty-five years, by far the longest duration for a bear bond market in US history If a constant maturity thirty-year 21 2% bond had been available throughout this second bear market of the century, its price would have declined from 101 in 1946 to 17 in 1981, or 83% In contrast, in the first bear bond market of the century, 1899 to 1920, the same bond would have declined 35% in price The recent bear bond market seemed to have much more social and economic significance than that of all earlier bear bond markets In all the others, bond yields stayed within the traditional band that had prevailed for centuries This time they broke decisively out of that band.

and accomplishes the same reaction as does the small-molecule reagent [Frechet et al., 1977; Johar et al., 1982]. Similar halogenating reagents are obtained from XXXIX (e.g.,

A Br , BrCl , ICl ) [Sket and Zupan, 1984]. An ethylene-N-bromomaleimide copoly2 2 3 mer has been used for bromine substitution at allylic and benzyl positions [Yaroslavsky et al., 1970]. Polymer Wittig reagents are useful for the conversion of an aldehyde or ketone to an alkene according to the sequence in Eq. 9-70 [Ford, 1986a,b].

Circuit at First Glance Step-by-Step Bending Choosing a Cool Control Layout Case Considerations Marking the Board Drilling Holes Painting Control Mounting Soldering Testing Reassembly Musicality 245 247 247 247 247 247 248 248 248 248 249 249.

9-70

The bear bond market of 1946 1981 can be subdivided into seven major price declines interspersed by six rallies These are summarized in terms of the monthly average of prime corporate bond yields and a corresponding price index for a constant maturity 21 2% bond in the table on page 368 The economic climate during the postwar period from 1946 to the mid-1960 s was favorable, often exuberant It was not until 1958 that inflationary expectations became highly articulate, and then for a while there developed something like a flight from bonds and from the dollar into gold, foreign currencies, or equities By 1961, stability was restored, and the inflation rate was negligible for the next five years In 1965, however, a dangerous inflationary spiral began and with it a superboom that was only briefly interrupted by a recession in 1970.

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