The possibility of preparation of cis-tris-σ-homobenzenes from cis-bis-σ-homobenzenes

Prinzbach, Horst; Böhm, Hans-Peter; Kagabu, Shinzo; Wessely, V.; Rivera, Henry Vera

doi:10.1016/s0040-4039(01)94512-5

Cited by 7 publications

(2 citation statements)

References 13 publications

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“…Subsequently, for both preparative and theoretical purposes, as probes for the concerted natures of the corresponding 3σ Ǟ 3π isomerization reactions, [33] the X,Y,Z components of A were systematically varied (X,Y,Z = O, [34,35] = NR, [36] = S, [37] = (CH 2 ) 2 [38] ), [39] the three-and four-membered rings were variously mixed [40] and variously bridged, [39,41,42] the six-membered backbones were modified (e.g., hexa-σ-/π-homobenzenes, [43] cis/trans-tropilidene (tropone)-(tri)oxides [44] ). Ultimately, through triple epoxide Ǟ cyclopropane conversions, stabilized derivatives (X,Y,Z = CHCO 2 R, CHCN) of the still unknown, kinetically highly labile parent hydrocarbon A (X,Y,Z = CH 2 ), could be secured.…”

Section: Discussionmentioning

confidence: 99%

In Pursuit ofcis,cis,cis‐Cyclonona‐2,5,8‐triene‐1,4,7‐trione – An Adventure in Medium‐Sized Ring Chemistry

et al. 2007

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Attempts to synthesize the long soughtafter tris‐π‐homobenzene cis,cis,cis‐2,5,8‐cyclononatriene‐1,4,7‐trione, via the newly prepared cyclononane‐1,4,7‐trione (C9H6O3), through base‐catalysed threefold HBr elimination from an efficiently prepared and stereochemically uniform tribromo derivative, failed due to typical medium‐ring complications, transannular reactions and an exceptional ease of polymerization. In the cations generated in the vapour phase through electron‐impact ionization (MS), the threefold elimination of (H)Br, competing with the elimination of CO, led to C9H7O3+ ions, whereas the impressively neat anionic three‐step fragmentation pathway resulted in C9H6O3– ion(s). Whilst the compositions of these bromine‐free ions, which were in part computationally approached {B3LYP/6‐31+G(d,p)}, and their assignments appeared compatible with the protonated and anionic target molecules, their true natures remain open. X‐ray structural analyses for several (bridged) nine‐membered ring compounds are provided. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Discussionmentioning

confidence: 99%

In Pursuit ofcis,cis,cis‐Cyclonona‐2,5,8‐triene‐1,4,7‐trione – An Adventure in Medium‐Sized Ring Chemistry

et al. 2007

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“…A number of groups have reported syntheses of compounds containing an aziridine adjacent to a cyclopropane ring ; however, the reactivity of only a few derivatives has been studied [20][21][22][23][24][25][26][27][28]. In particular, it has been shown that the aziridine can be hydrogenated without affecting the cyclopropane moiety in the molecule [29,30].…”

Section: Introductionmentioning

confidence: 99%

Cyclopropyl aziridines: solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

Silverberg

Rabb

Reno

et al. 2014

Heterocyclic Communications

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The N-tosylaziridine 4 of (+)-2-carene 1 was prepared and subjected to solvolytic reactions with weak protic acids. For comparison, the solvolytic reactions of cis-3-carene-N-tosylaziridine 8 were also studied. The solvolyses of 4 were more rapid than those of 8, and both rings were opened in 4, whereas only the aziridine was opened in 8. This leads to the conclusion that the aziridine and cyclopropane rings in 4 can achieve a conjugated transition state.

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Cyclic Sulfides

Capozzi

and

Nativi

1995

PATAI'S Chemistry of Functional Groups

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The possibility of preparation of cis-tris-σ-homobenzenes from cis-bis-σ-homobenzenes

Cited by 7 publications

References 13 publications

In Pursuit ofcis,cis,cis‐Cyclonona‐2,5,8‐triene‐1,4,7‐trione – An Adventure in Medium‐Sized Ring Chemistry

In Pursuit ofcis,cis,cis‐Cyclonona‐2,5,8‐triene‐1,4,7‐trione – An Adventure in Medium‐Sized Ring Chemistry

Cyclopropyl aziridines: solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

Cyclic Sulfides

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