Unsaturated heterocyclic systems. LXXIII. .pi.-Equivalent heterocyclic congeners of cyclooctatetraene. Synthesis and valance isomerization of 2-alkoxyazocines

Paquette, Leo A.; Kakihana, Tsuyoshi; Hansen, John F.; Philips, J. Christopher

doi:10.1021/ja00730a027

Cited by 39 publications

(9 citation statements)

References 3 publications

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“…The compound was in fact thermally stable.180 The reaction is photochemically allowed, and irradiation indeed caused fragmentation to occur.180 It is of interest also that, in the case of 47, naphthalene is formed both thermally and photochemically.20 Insofar as 51 is formed on alkaline dehydrobromination of 50, it is also most unstable thermally, as naphthalene, rather than 51, is produced. 21 The results which are more germane to this Account involve precursors other than 49 or 50. They involve 52 as starting material, and this was produced in a Diels-Alder reaction of 1,2-dimethyl cyclobutenedicarboxylate and butadiene (Scheme V).…”

Section: Ch3mentioning

confidence: 92%

Small-ring propellanes

Ginsburg¹

1972

Acc. Chem. Res.

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Slowly but surely the propellane nomenclature is being accepted.1Propellanes have been defined as tricyclic systems conjoined "in"2 or "by"3 a carbon-carbon single bond. In this Account we shall discuss only smallring propellanes, defined herein as those which contain five to ten carbon atoms in their carbocyclic skeleton.4Obviously, heterocyclic propellanes having, say, eight carbon atoms in their skeleton are of larger ring size than corresponding carbocyclic propellanes which may, at least on paper, potentially be produced from

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Section: Ch3mentioning

confidence: 92%

Small-ring propellanes

Ginsburg¹

1972

Acc. Chem. Res.

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“…mixture was carefully added to 1 N hydrochloric acid and tetrahydrofuran. 11 The unsaturated lactam so produced (6) was catalytically hydrogenated to give iV-methylcaprolactam, spectroscopically identical with an authentic sample.…”

mentioning

confidence: 86%

“…The latter phenomenon has in fact contributed to the widespread success of the diaza-Cope rearrangement.19 •20 In any case, it is now quite clear that imidates do not enter into electrocyclic rearrangements with a facility equal to their isoconjugate olefinic counterparts.21 This information is used to mechanistic advantage in the accompanying communication.22 (10) Characterized also as to composition by mass spectral and combustion analyses. (11) Hydrolysis with water gave 6 accompanied by a second product tentatively identified as methyl c/s-6-methylaminohex-4-enoate. ( 12 folded rather than an extended molecular conformation,3 the difficulties have consisted in reconciling stereochemical and kinetic fact with orbital symmetry theory and in disregarding the several other nonrelevant structural changes which operate concurrently.…”

mentioning

confidence: 99%

Thermal isomerization of homoazocines

Ewing¹,

Ley²,

Paquette³

1978

J. Am. Chem. Soc.

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“…The cycloaddition of CSI with 1,4-dihydrobenzene derivatives has been used as the first step in the synthesis of 2alkoxyazocines. 35 For example, 93 was obtained by the se-…”

Section: Other Monoterpene Olefinsmentioning

confidence: 99%