Volume 11, Fiesers' Reagents for Organic Synthesis by Mary Fieser

By Mary Fieser

This quantity covers reagent literature released among July 1981 and December 1982. It presents references to new reagents brought in this interval, in addition to fresh references to reagents incorporated in prior volumes, targeting reagents that open new vistas in natural synthesis.

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Higher atomic mass precedes lower atomic mass. 3. Cis (Z) precedes trans (E). Some special cases require the following qualification [149]: when two ligands (indistinguishable by rules 1 and 2) differ by one having the ligand of higher rank in a cis position (Z) to the core of the stereogenic unit, and the other in a trans position (E), the former takes precedence. 4. Like pair precedes unlike pair. (For a listing of like and unlike pairs, see l,u in this glossary). 5. R precedes S, and M precedes P To implement the sequence rules, it is useful to construct a digraph of the ligands to be compared, as shown below.

E. Chirality made simple: A 1- and 2-dimensional introduction to stereochemistry. J. Chem. Educ. 2005, 82, 1009À1012. 11 GLOSSARY OF STEREOCHEMICAL TERMS22 G L O S S A R Y A values The free energy difference ( 2 ΔG ) between equatorial and axial conformations of a substituted cyclohexane, positive if equatorial is preferred. 9. For a compilation of values, see ref. [125,126] and references cited therein. A1,2, A1,3 strain see allylic strain. Absolute asymmetric synthesis A synthesis in which achiral reactants are converted to nonracemic, chiral products, and where the enantioselectivity is induced only by an external force such as circularly polarized light in a photochemical reaction [127].

If the reference plane is horizontal, β is above and α is below the plane, as illustrated below. If the plane is vertical, β is toward the viewer. In carbohydrates, the β-anomer has the hydroxyl or alkoxyl group at C1 (circled) on the opposite side of a Fischer projection as the substituent (*) that defines D or L (see FischerÀRosanoff convention); this need not be the position at which the ring is closed. The α-anomer has the two on the same side [130]. 22. Note that the terms defined in this glossary are italicized.

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