ISBN-10: 0470187204

ISBN-13: 9780470187203

ISBN-10: 0471056243

ISBN-13: 9780471056249

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 ok. 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

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669 ArCHCH CO R 21)) (i-Pr),NLi I,, - 7 8 O I * ArCH$yZR 0 OH The intermediate in the reaction is presumably complex 90 produced from the enolate of the 0-hydroxyester. R O A ; 0.. Lf Li 90 Oxiranes may also be prepared from the reaction of aldehydes with trivalent phosphorus derivatives, as in Eq. 97. 2 ArCHO + (R2N)3P - A r T Ar + (R2N)3P=0 (97) 0 The interpretation of the mechanism of the reaction is that the trivalent phosphorus attacks the oxygen of the aldehyde, after which diastereomeric dioxaalkane intermediates 91,92 are obtained with another molecule of aldehyde.

Bromoalcohols are produced from alkenes with N-bromosuccinimide or N-bromoacetamide, while iodoalcohols are prepared with iodine in the presence of oxidants (iodic acid, oxygen, and nitrite). Synthesis of Oxiranes 41 The hydroxy function may originate from the reduction of an a-halogenated carbonyl compound or a Grignard reaction. The oxirane oxygen is not always incorporated directly from a hydroxy group; for instance, in the case of a carboxylic acid ester, it is derived with neighboring-group participation from an ortho-monoester intermediate.

Lf Li 90 Oxiranes may also be prepared from the reaction of aldehydes with trivalent phosphorus derivatives, as in Eq. 97. 2 ArCHO + (R2N)3P - A r T Ar + (R2N)3P=0 (97) 0 The interpretation of the mechanism of the reaction is that the trivalent phosphorus attacks the oxygen of the aldehyde, after which diastereomeric dioxaalkane intermediates 91,92 are obtained with another molecule of aldehyde. 670,671 The mechanism of a-halooxirane formation is illustrated in Eq. 98. Reactions of Oxiranes (Me,N),P R' + R'CCl, - 0 (Me,NI3P I 0 C-R I c1 c1, - 57 R21C,0 H' (98) = C 0 2 R , CONHz It has been established that the alcoholates formed are very reactive.

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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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