The stereoselective synthesis of functionalized conjugated dienes : preparation of (E,E)-α-hydroxy dienes and of vinylallenes.

Bloch, Robert J.; Hassan, Dheefaf F.; MANDARD, X.

doi:10.1016/s0040-4039(00)86229-2

Cited by 23 publications

(1 citation statement)

References 7 publications

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“…The substituted 3-sulfolenes are well-known key precursors of not only different sulfolanes, 26,27 polycyclic heterocycles 28 but also conjugated unsaturated compounds. 29,30 The thermal extrusion of SO 2 (temperatures typically >100 °C) from these stable compounds provides corresponding 1,3-dienes. 31…”

Section: Introductionmentioning

confidence: 99%

Highly efficient synthesis of 3,4-diarylbutadiene sulfones using Heck–Matsuda reaction

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Section: Introductionmentioning

confidence: 99%

Highly efficient synthesis of 3,4-diarylbutadiene sulfones using Heck–Matsuda reaction

et al. 2022

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ThePeterson Olefination Reaction

Ager¹

1990

Organic Reactions

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The Peterson olefination reaction provides a useful method for the preparation of alkenes from α‐silyl carbanions and carbonyl compounds. As alkenes hold a pivotal role in synthetic methodology for the introduction of vicinal functionality, particularly in a stereoselective manner, the Peterson reaction is increasing in importance in the reaction repertoire. This chapter discusses the reaction and its advantages over comparable methods such as the Wittig reaction. Although elimination of β‐silylalkoxides, was noted in 1947, it was not until Peterson described the preparation of functionalized alkenes from α‐silyl carbanions in 1968 that the full potential of the reaction became apparent. Alkenes are usually only isolated directly from the condensation when an anion‐stabilizing group is present in the carbanion; if not, the β‐hydroxysilane is formed. Many examples of the formation of alkenes from β‐hydroxysilanes are cited in the literature. These eliminations are discussed in this chapter, although they strictly should not be called Peterson olefination reactions. However, the “common” organic reactions of β‐hydroxysilanes which follow the usual pathways—such as the thermolytic elimination of esters derived from those alcohols—are omitted. The central nature of the Peterson reaction to organosilicon chemistry has led all reviews in this area to discuss the subject to some extent. In addition, the reaction itself has been reviewed previously.

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The Retro–Diels–Alder Reaction PartI.CCDienophiles

Rickborn

1998

Organic Reactions

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The Diels–Alder (“DA”) reaction is so familiar to organic chemists that the retro‐Diels–Alder or retro‐diene reaction (hereafter “rDA”) requires no conceptual introduction. However, a working definition is needed to indicate the coverage of this review. The intent is to include all reported examples of the general skeletal process excluded in this chapter. Any of the atoms in the starting material (cycloadduct) may be carbon or heteroatom, and substituents on all positions are allowed. In addition, any bond order available to the element in any oxidation state is included, as well as bonding to non‐nearest neighbor atoms (bicyclics, etc.). The volume of literature required separation of this review into two parts. Part I covers all expelled C–C dienophiles, i.e. those reactions that generate a new carbon‐carbon double or triple bond in the dienophile that is formed. Part II, to appear later, covers those expelled dienophiles in which one or both atoms is a heteroatom. Certain specific topics are intentionally omitted. These are: rDA reactions invoked under mass spectral conditions; rDA reactions of polymeric substrates; Electrocyclic processes, some of which are arguably very similar to rDA reactions (these are not addressed unless needed for clarification of an rDA sequence); and a thorough discussion of homo‐rDA reactions. CAS‐Online searches resulted in ca. 1,300 references, of which ca. 900 proved pertinent to the rDA topic as defined and delimited above. Active literature searching was halted in April 1995, but occasional more recent articles are included. Over 2,500 pertinent references were eventually found. Most were obtained by perusal of primary literature (articles) and secondary sources (books and reviews). Computer based search success was limited mainly by the failure of authors or abstractors to key‐word this topic, an especially common occurrence when the expelled dienophile was a simple substance such as N 2 or CO 2 . Overall, approximately 3,500 books, chapters, reviews, articles, and abstracts were consulted in an effort to make this review as comprehensive as possible. This was done with the certainty that some pertinent literature would be missed, tempered by the view that these omissions are probably also lost to any future rational search method. Many secondary sources proved valuable not only for in‐depth discussion of certain rDA reaction types, but also for providing comparisons with related topics. To assist the reader, these secondary sources are referenced (alphabetically by first author within broad subject areas) with a title or brief note on the topic(s) addressed. The first group lists earlier reviews with primary focus on rDA reactions, followed by items of Historical/General Interest, reviews that deal with Experimental Methods, DA reactions (general and specific), reviews of Related Topics (these impinge in more or less significant ways on rDA reactions), and general treatments of Theory and Mechanism.

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The stereoselective synthesis of functionalized conjugated dienes : preparation of (E,E)-α-hydroxy dienes and of vinylallenes.

Cited by 23 publications

References 7 publications

Highly efficient synthesis of 3,4-diarylbutadiene sulfones using Heck–Matsuda reaction

Highly efficient synthesis of 3,4-diarylbutadiene sulfones using Heck–Matsuda reaction

ThePeterson Olefination Reaction

The Retro–Diels–Alder Reaction PartI.CCDienophiles

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