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

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 material: bankruptcy I Oxiranes (pages 1–196): M.

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

Sample text

297,298 The experimental results have led to the proposal of a 1,3-dipolar addition mechanism, the molybdenum atom being involved directly (Eq. 28). ’~’Further kinetic studies suggest the structure of the transition complex shown in Eq. 29. 303 From cis- and trans-olefins the main product is the trans isomer, formed via a biradical intermediate. Cholesterol undergoes f l - e p o x i d a t i ~ n . ~ ~ Boron-containing catalysts have also found a p p l i ~ a t i o n , with ~ ~ ~a- relatively ~~~ lower stereoselectivity.

26). A fair number of articles have recently dealt with the kinetics and mechanism of the r e a ~ t i o n . 2m The method is of great promise in industrial synthe. has the advantage that the side-product of the reaction is water. ”~Detailed studies have been made on the mechanism of the reaction of the Mo0(02),-HMPT complex with olefins (Eq. 297,298 The experimental results have led to the proposal of a 1,3-dipolar addition mechanism, the molybdenum atom being involved directly (Eq. 28). ’~’Further kinetic studies suggest the structure of the transition complex shown in Eq.

672 X = C1, Br, C1O4 L = pyridine, etc. , Cu(OCH3)Clpyridine) (Eq. 673 IV. REACTIONS OF OXIRANES The chemical behavior of oxiranes is governed by two factors: the strain in the ring and the basicity of the ring. The extent to which these two factors contribute to the reactivity, either separately or jointly, can be assessed from the results of the reaction under various conditions. The reactions generally involve heterolytic opening of the C-0 bond (Eq. 100, 1). This opening, most often induced by an electrophile, is accompanied by attack from a nucleophile (a) or a 1,2-rearrangement (b).

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