Thermolysereaktionen gespannter Verbindungen: Mechanistische Deutung und synthetische Nutzung

Griesbeck, Axel G.

doi:10.1002/prac.19933350602

Cited by 6 publications

(3 citation statements)

References 100 publications

(7 reference statements)

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“…Further transformations of the triquinane 277 led to (-)-212. Elaboration of the protected dihydroxydienone 278 resulted in the total synthesis of natural (+)-coriolin-B (274).…”

Section: Coriolin and Hypnophilinmentioning

confidence: 99%

“…Griesbeck and co-workers 273,274 have explored a variation of the photo thermal metathesis theme developed by Mehta et al, 270 for the synthesis of a tetraquinane framework present in crinipellins (Scheme 141). The Diels-Alder reaction of the tetrahydropentalene 531 with p-benzoquinone followed by intramolecular [2+2]-photocycloaddition and flash vacuum pyrolysis furnished the tetraquinane bisenone 532.…”

Section: T H Imentioning

confidence: 99%

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Synthesis of Polyquinane Natural Products: An Update

1997

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“…Further transformations of the triquinane 277 led to (-)-212. Elaboration of the protected dihydroxydienone 278 resulted in the total synthesis of natural (+)-coriolin-B (274).…”

Section: Coriolin and Hypnophilinmentioning

confidence: 99%

Section: T H Imentioning

confidence: 99%

Synthesis of Polyquinane Natural Products: An Update

1997

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“…In contrast, the ligand of 27, benzocyclobutene, has been known for about 40 years now, and its chemistry is well investigated. Many derivatives are known and have been used to prepare theoretically interesting compounds or natural products, [17][18][19][20][21][22][23][24][25][26][27][28][29] and a number of theoretical calculations have been carried out in this field. [30][31][32][33][34][35][36][37][38][39][40][41] Another difference between 5 and 27 is the fact that the ligand of 5 is an anion whereas benzocyclobutene is electroneutral.…”

Section: Benzocyclobutene Complexesmentioning

confidence: 99%

π Complexes with Annellated Cyclobutene Rings: Bicyclo[3.2.0]heptadienyl Anion and Benzocyclobutene as Ligands for Transition Metals

Butenschön¹

1999

Synlett

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As was first found on the basis of DSC measurements, bicyclo[3.2.0]heptadienyl cobalt complex 17 undergoes a ring opening -cycloaddition sequence at high temperature with formation of ring expansion products. Benzocyclobutene complexes react in a similar way only in one case. However, deprotonation of benzocyclobutenol complex endo-31 results in a dramatic decrease of the ring opening temperature and allows corresponding [4+2] cycloaddition reactions at low temperature. Benzocyclobutenedione complex 74 shows interesting structural features, its fragmentation in the mass spectrometer leads to a η 6 coordinated benzyne chromium cation. Addition of vinylmetal reagents induces a dianionic oxy-Cope rearrangement at -78°C, the first case of such a reaction at such mild reaction conditions. Products are benzannellated cyclooctenediones and their intramolecular aldol adducts, which are obtained with very high diastereoselectivity.

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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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Thermolysereaktionen gespannter Verbindungen: Mechanistische Deutung und synthetische Nutzung

Cited by 6 publications

References 100 publications

Synthesis of Polyquinane Natural Products: An Update

Synthesis of Polyquinane Natural Products: An Update

π Complexes with Annellated Cyclobutene Rings: Bicyclo[3.2.0]heptadienyl Anion and Benzocyclobutene as Ligands for Transition Metals

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

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