Chemistry of Heterocyclic Compounds: Small Ring

Oxiranes (M. Bartok and okay. Lang).

Arene Oxides-Oxpins (D. Boyd and D. Jerina).

Oxaziridines (M. Haddadin and J. Freeman).

Dioxetanes and a-Peroxylactones (W. Adam and F. Yany).

4-membered Sulfur Heterocycles (D. Dittmer and T. Sedergran).

writer and topic Indexes.Content:
Chapter I Oxiranes (pages 1–196): M. Bartok and okay. L. Lang
Chapter II Arene Oxides?Oxepins (pages 197–282): Derek R. Boyd and Donald M. Jerina
Chapter III Oxaziridines (pages 283–350): Makhluf J. Haddadin and Jeremiah P. Freeman
Chapter IV 1,2?Dioxetanes and ??Peroxylactones (pages 351–429): Waldemar Adam and Faris Yany
Chapter V Four?Membered Sulfur Heterocycles (pages 431–768): D. C. Dittmer and T. C. Sedergran

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Extra resources for Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others, Volume 42

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666 A general method has been elaborated for the preparation of 1,2-epoxyalkane phosphonates starting from 1-chloro-1-lithioalkane phosphonates produced by chloro-lithium exchange from a 1,l-dichloro derivative (Eq. 668The prophosphoncedure is also suitable for the synthesis of l-substituted-1,2-epoxyalkane ates (Eq. 668 T '\P-CH2 X' I C1 89 Y = 0,S X = EtO, (CH3)2N Oxiranes 56 0 EtO, /I EtO/P-CH2C1 1) n-BuLi - 70° 7 + ~ 70", o Et0,ll ,P EtO 20° 0 Me Me -cI1 -c 1 EtO' Li (95) This reaction also can be effected in one step without the isolation of an intermediate.

Many researchers are still occupied with the elucidation of the mechanism of the reaction. 151,275, 329-333 Th e large amount of experimental work that has been performed provides a possibility for establishing favorable conditions of epoxidation with regard to the roles of the catalyst, the organic hydroperoxide, the structure of the olefin, and the medium. Similar to the hydrogen peroxide-transition-metal complex reaction, this is an electrophilic reaction (Eq. 334 Application of the organic hydroperoxide in the reaction leads to many advantages.

Accordingly, one major oxirane isomer is formed (Eq. 518 Stereospecific epoxidation of olefins with radical 6 2 , produced in a mixture of tetramethyltetrazene-ZnCl’ and oxygen, is a radical-catalyzed p r o c e ~ s . ’’~-”~The peracid oxidation is stereospecific. ’’~ E. Other Oxidation Methods The epoxidation procedures described here are not general ones; they are used in special cases to prepare stereoisomers that are difficult to obtain by other means. 2,4-Disubstituted-6-hydroxymethylphenols have been oxidized with good yields t o spirooxirane derivatives with sodium periodate in the case of bulky substituents, for example, when R’ = R’ = tert-butyl (Eq.

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