Systems Capable of 1,4-Cycloaddition Reactions

Hamer, Jan

doi:10.1016/b978-0-12-395743-6.50006-5

Cited by 24 publications

(38 citation statements)

References 21 publications

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“…An analogous reaction occurred with diphenyl isobenzofuran, giving the corresponding diketone in 75% yield. Compound l b reacted with substituted butadienes gave in good yields stable adducts with oxazine structures 19a-c. Their spectroscopic characteristics (Table 3) are similar to those of this type of compound [2] [33]. We observed high regioselectivity in the case of 19c where only one isomer was formed.…”

Section: M+supporting

confidence: 70%

“…Nitrosoalkenes possess a large synthetic potential, since they comprise both an alkene activated by an electron withdrawing group and an 1,3-diene system. Furthermore, the nitroso group itself reacts with it wide number of reagents [l] and allows an easy, simultaneous incorporation of nitrogen and oxygen by addition reactions (Diels-A lder [2], ene-reaction [3] and ( 2 + 2)-cycloaddition [4]). However, despite the obvious interest of nitrosoalkenes, the first to be isolated (nitrosocyclohexene) was reported only in 1967 [ 5 ] .…”

Section: Discussionmentioning

confidence: 99%

“…The dienophilic character of electron deficient nitroso compounds has long been known. Tertiary aliphatic nitroso compounds substituted by electronwithdrawing groups and most nitroso-aromatic compounds react rapidly with dienes to form moderately stable oxazine derivatives [2].…”

Section: Discussionmentioning

confidence: 99%

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Nitrosoalkenes: Synthesis and Reactivity

Francotte

Merényi

Vandenbulcke-Coyette

et al. 1981

Helvetica Chimica Acta

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SummarySome (1-and 8-halonitrosoalkenes 1 have been synthesized and characterized. The halogen atoms of the oxime precursors 2 can be substituted by alkoxy groups. Two kinds of cycloaddition reaction of 1 have been observed: i) reaction of the NO group with dienes gives 3,6-dihydrooxazine derivatives 6 which isomerise to epoxyepimines 7 in most cases of 8-substituted nitrosoalkenes: ii) if 4,5-dihydrooxazines 22 are obtained, the cycloaddition of the nitrosoalkenes as 4 7r-component is presumed.Nitrosoalkenes possess a large synthetic potential, since they comprise both an alkene activated by an electron withdrawing group and an 1,3-diene system. Furthermore, the nitroso group itself reacts with it wide number of reagents [l] and allows an easy, simultaneous incorporation of nitrogen and oxygen by addition We have recently reported the epoxy-epimination of cyclic 1,3-dienes by isomerization of the cycloadducts formed from such dienes with certain halonitrosoalkenes [6] [7]. This reaction merits particular attention since nitrosoalkenes are readily accessible, highly reactive intermediates which can be used in situ. In order to study the scope and limitations of this stereospecific reaction, which allows the functionalization of the four sp2-centres of a diene in one step, it seemed interesting to vary the dienes and the substituents of the nitrosoalkene.') Taken in part from the Ph. D-Thesis of E. Francotte (l078), present address: C'iha-Geigy AG, Zentrale Forschung. CH-4002 Basel.0018-019X/81/4/1208-11$01.00/0 0 198 I Schweizer-ische Chemiache Gesellschaft

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Section: M+supporting

confidence: 70%

Section: Discussionmentioning

confidence: 99%

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Nitrosoalkenes: Synthesis and Reactivity

Francotte

Merényi

Vandenbulcke-Coyette

et al. 1981

Helvetica Chimica Acta

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“…An attractive method for the desired modifications was to use the Diels-Alder (1,4-cycloaddition) reaction (Hamer, 1967) of dienophiles with the suitably oriented 1,3-diene system in (E)-fl-farnesene. With various dienophiles, products could be obtained with different stabilities, volatilities, and polarities, so that factors influencing activity could be recognized.…”

Section: Introductionmentioning

confidence: 99%

Aphid alarm pheromone derivatives affecting settling and transmission of plant viruses

et al. 1982

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1,4-Cycloaddition reactions between (E)-β-farnesene (the aphid alarm pheromone) and dienophiles, such as SO2 and RO·CO·C ≡ CCO·OR, gave products more stable and less volatile than the parent compound. In laboratory experiments, the numbers ofMyzus persicae (Sulz.) settling and nymphs deposited on plants were decreased by some of the reaction products. Acquisition, and thereby transmission, of the semipersistent beet yellows virus and the nonpersistent potato virus Y, was decreased.

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“…0,9758 (4) O (6) 0,829 l(3) O (7) 1,1486(3) O (8) 0,6842(3) O (9) 0,8523 (4) O (10) 1,0033(4) N (1) 0,8619(3) N (2) 0,8558(3) N (3) 0,9002(4) N (4) 0,9098(3) N (5) 0,9108(3) N (6) 0,9252(4) C (1) 0,7233(4) C (2) 1,0029(4) C (3) 0,9864(4) C (4) 0,8671(4) C (5) 0,8849(4) C (6) 0,8875(5) C (7) 0.8719 (5 …”

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Diels‐Alder‐Reaktionen von 2,4‐Bis{[(tert‐butyl)dimethylsilyl]oxy}‐3‐aza‐1,3‐pentadien mit Heterodienophilen

Ried

Reiher

Jan

1987

Helvetica Chimica Acta

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Diels-Alder Reactions of 2,4-Bis{ [(tert-butyl)dimethylsilyl~oxy}-3-aza-l,3-pentadien with HeterodienophilesThe 2,4-bis{ [(tert-butyl)dimethylsilyl]oxy~-3-aza-l,3-pentadien (2) reacts via the Diels-Alder adducts 3, 6a<, and 8a, b,which cannot be isolated, giving the triazines 4, 7a-c, and the oxadiazines 9a, b. The hydrolysis of 4 in MeOH affords the N-acetyl-acetamid derivative 5. The formula of 9a is proven by an X-ray-structure analysis.Einleitung. -

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Systems Capable of 1,4-Cycloaddition Reactions

Cited by 24 publications

References 21 publications

Nitrosoalkenes: Synthesis and Reactivity

Nitrosoalkenes: Synthesis and Reactivity

Aphid alarm pheromone derivatives affecting settling and transmission of plant viruses

Diels‐Alder‐Reaktionen von 2,4‐Bis{[(tert‐butyl)dimethylsilyl]oxy}‐3‐aza‐1,3‐pentadien mit Heterodienophilen

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