Thermal Rearrangements of Heteroatom‐Bridged Diallenes

Bui, Binh H.; Schreiner, Peter R.

doi:10.1002/ejoc.200600270

Cited by 8 publications

(7 citation statements)

References 40 publications

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“…Application of these principles led to Bergman-like cyclizations of 3-substituted 1,4-pentadiynes, 58 Myers-Saito reactions leading to hetero-cyclopentadiendiyl derivatives, 59 the cyclization of Moore's enynes-ketenes to oxo-heterocyclopentadiendiyl, 60 and diallenes to hetero-3,4-dimethylenecyclopentadienediyl derivatives. 57 True predictions were made and it is encouraging to see that some were proven experimentally in the meantime, 61,62 as well as the formation of anions of fulvenes and fulvalene derivatives from cross-conjugated enediynes. 62 The enlargement of the heuristic concept to heteroatom-systems increased the number of possible reactions that exhibit comparable properties, and that might be of interest for synthetic chemistry or for studies investigating their DNA cleavage abilities.…”

Section: A Case Study: Pericyclic Reactions-the Six Electron Casementioning

confidence: 93%

Heuristic thinking makes a chemist smart

2010

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We focus on the virtually neglected use of heuristic principles in understanding and teaching of organic chemistry. As human thinking is not comparable to computer systems employing factual knowledge and algorithms--people rarely make decisions through careful considerations of every possible event and its probability, risks or usefulness--research in science and teaching must include psychological aspects of the human decision making processes. Intuitive analogical and associative reasoning and the ability to categorize unexpected findings typically demonstrated by experienced chemists should be made accessible to young learners through heuristic concepts. The psychology of cognition defines heuristics as strategies that guide human problem-solving and deciding procedures, for example with patterns, analogies, or prototypes. Since research in the field of artificial intelligence and current studies in the psychology of cognition have provided evidence for the usefulness of heuristics in discovery, the status of heuristics has grown into something useful and teachable. In this tutorial review, we present a heuristic analysis of a familiar fundamental process in organic chemistry--the cyclic six-electron case, and we show that this approach leads to a more conceptual insight in understanding, as well as in teaching and learning.

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Section: A Case Study: Pericyclic Reactions-the Six Electron Casementioning

confidence: 93%

Heuristic thinking makes a chemist smart

2010

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“…[25] Ther-mal rearrangements of heteroatom-bridged diallenes have also been reported. [26] Although diallenes can be easily and even quantitatively transformed into bis(alkylidene)cyclobutenes, the formation of diallenes is harder to explain. Within this framework, the problem of the formation of F is shifted to a possible reaction pathway able to explain the formation of a diallene.…”

Section: Mechanistic Considerationsmentioning

confidence: 99%

The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

et al. 2011

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International audienceHerein we describe the synthesis of new substituted tetraaryltetracenes, obtained by the dimerization of triarylchloroallenes, prepared from propargyl alcohols. The propargyl alcohols were prepared by two different synthetic strategies and then the alcohols were treated to obtain the corresponding acenes. In addition to the expected tetracene derivatives, we observed the formation of bis(alkylidene)cyclobutenes. When strong electron-donating substituents were present, the main product was the cyclobutene. We discuss a reaction mechanism that accounts for the formation of the cyclobutenes

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“…The generation and chemical behavior of many heterorganic acyclic bisallenes is summarized in Scheme 116 and basically consists of three steps [269]. In the first step the bisallene 522 is generated from a usually readily available diacetylene 521 by base treatment.…”

Section: Reviewmentioning

confidence: 99%

The chemistry of bisallenes

Hopf¹,

Μαρκόπουλος²

2012

Beilstein J. Org. Chem.

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SummaryThis review describes the preparation, structural properties and the use of bisallenes in organic synthesis for the first time. All classes of compounds containing at least two allene moieties are considered, starting from simple conjugated bisallenes and ending with allenes in which the two cumulenic units are connected by complex polycyclic ring systems, heteroatoms and/or heteroatom-containing tethers. Preparatively the bisallenes are especially useful in isomerization and cycloaddition reactions of all kinds leading to the respective target molecules with high atom economy and often in high yield. Bisallenes are hence substrates for generating molecular complexity in a small number of steps (high step economy).

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Thermal Rearrangements of Heteroatom‐Bridged Diallenes

Cited by 8 publications

References 40 publications

Heuristic thinking makes a chemist smart

Heuristic thinking makes a chemist smart

The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

The chemistry of bisallenes

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