Oxiranes (M. Bartok and ok. 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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Additional resources for Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others, Volume 42
The sulfonium ylides also react with other types of compounds containing an electrophilic unsaturated bond (C=C, C=N), giving cyclopropane derivatives and aziridines. 624 Reactive ylides are prepared from dialkyl sulfide and dialkyl sulfoxide in a nonaqueous medium. ^^' While the mechanism of the reaction has been clarified in accordance with the scheme outlined in Eq. 89,628-631its stereochemistry is not known in every respect. The sulfoxonium ylides are more stable and behave as better leaving groups than the sulfonium ylides.
600 + R-CH-COzEt I Br Ryy R' RZ fi' \I p780ce RZ 0 + RR R' COzEt (75) COzEt a-Haloglycidates 74 have been obtained from dihalo esters. 60"602In a protic medium, dichloroacetonitrile gave a-haloglycidimic esters (Eq. 603 CHC1,CN + R R' // C 8 R 0 C1 f l ,0-i-Pr i-PrOH i-PrOK- (76) NH The preparation of glycidic nitriles has also been described under phase-transfer conditions (Eq. 6Mb Formation of diazoketoxiranes is shown in Eq. 605 0 ClCHz-C-CHN, + Ph-CHO *::: PhLC-CHN, (78) II 0 6 The trans-epoxysulfone is exclusively produced from toluylchloromethylsulfone; the stereoselectivity is motivated by solvation and steric reasons (Eq.
When the double bond is not so electron-poor, epoxidation can be achieved with hydrogen peroxide in the presence of a transitionmetal catalyst. a. OXIDATION WITH ALKALINE HYDROGEN PEROXIDE This method was first described by Weitz and S ~ h e f f e r . ’The ~ ~ oxidation begins with a reversible attack by the nucleophilic hydroperoxy anion on the conjugated system, and an oxirane conjugated with an electron-attracting group is formed by ring-closure following the loss of OH- from the intermediate enolate anion (Eq.