Organic photochemistry. 16. Photochemical hydrogen abstraction reactions proceeding through five-membered transition states. Product control through restriction of rotation in diradical intermediates

Scheffer, John R.; Jennings, Barry M.; Louwerens, John P.

doi:10.1021/ja00438a051

Cited by 19 publications

(13 citation statements)

References 13 publications

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“…All six-membered rings have half-chair conformation, as predicted for cyclohexene by minimum-energy calculations (Bucourt & Hainaut, 1965). The largest deviations from these calculated values occur for the (IIa) -4a,5,8,8a-tetrahydro-l,4-naphthoquinone [(I) in Table 1] and its derivatives, in solution (Scheffer, Jennings & Louwerens, 1976) and the solid state (Dzakpasu, Phillips, Scheffer & Trotter, 1976), has revealed unusual reaction pathways. Photolysis of (I) in solution gives products resulting from intramolecular /3-H abstraction.…”

Section: Resultsmentioning

confidence: 99%

“…A study of the photochemistry of various substituted cis-4a,5 ,8,8a-tetrahydro-l ,4-naphthoquinone systems in solution (Scheffer, Jennings & Louwerens, 1976) and the solid state (Dzakpasu, Phillips, Scheffer & Trotter, 1976) has revealed unusual reaction pathways. The solid-state dimerization of 5a,8a-dimethyl-4a/3,5,8,8afl-tetrahydro-l,4-naphthoquinone (Ic) has been described and the crystal structure determined, together with that of the dimer product (IIc) (Phillips & Trotter, 1977a).…”

Section: Introductionmentioning

confidence: 99%

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The crystal and molecular structures of solid-state photodimers of two cis-4a,5,8,8a-tetrahydro-1,4-naphthoquinone derivatives

Phillips¹,

Trotter²

1977

Acta Crystallogr Sect B

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The crystal and molecular structures of solid-state photodimers of two cis-4a,5,8,8a-tetrahydro-1,4-naphthoquinone derivatives

Phillips¹,

Trotter²

1977

Acta Crystallogr Sect B

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“…cyclic as well as acvclic 1 -3-dienes have served. as a result of their photochemical rearrangements, as a rich source of novel polycyclic ring systems (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13). Three representative examples are shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Trapping of o-quinodimethane with p-quinones: synthesis of tetrahydro-1,4-anthracenediones

Askari¹,

Lee²,

Perkins³

et al. 1985

Can. J. Chem.

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. Can. J. Chem. 63, 3526 (1985). Previous work from our laboratory has been concerned with investigating the photochemical reactivity of the tetrahydro-1,4-napthalenedione system, both in solution and the solid state. The results obtained prompted us to extend our studies to the analogous tetrahydro-l,4-anthracenedione system. The most direct method of synthesis of the desired compounds is through Diels-Alder addition of o-quinodimethane to p-quinones. Because of the ease with which the adducts would be expected to undergo bis-enolization to the corresponding hydroquinones, their preparation requires mild, neutral conditions. After much experimentation, success was achieved using the Durst-Charlton sulfur dioxide extrusion method for generating o-quinodimethane from 3,6-dihydro-l,2-oxathiin-2-oxide. In situ trapping.using p-benzoquinone and other substituted p-quinones afforded the desired adducts in reasonable yields. In the case of duroquinone and 2,3-dimethyl-l,4-naphthalenedione, fluoride ion-catalyzed generation of o-quinodimethane from [o-[cu-(trimethylsilyl)methyl]benzyl]trimethylamrnoniurn bromide by the method of Ito also gave acceptable results; however, the bis-enolizable adducts were not stable under these eaction conditions. SYED ASKARI, SUSAN LEE, ROBERT R. PERKINS et JOHN R. SCHEFFER. Can. J. Chem. 63, 3526 (1985). Dans un travail anttrieur rtalist dans notre laboratoire, on a examine la rtactivitt photochimique du systeme titrahydronaphtalbnedione-1,4 tant en solution qu'a l'ttat solide. Les rtsultats obtenus nous ont incitt a Ctendre nos ttudes au systbrne analogue de la tttrahydroanthracenedione-1,4. La rntthode la plus directe de synthese des composts dtsirts implique une addition de Diels-Alder du o-quinodimtthane sur des p-quinones. Compte tenu du fait qu'il est A prCvoir que les adduits subiront facilement une bis-enolisation conduisant aux hydroquinones correspondantes, il est important d'utiliser des conditions

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“…A study of the photochemistry of eis-4a,5,8,8a-tetrahydro-l,4-naphthoquinone [(I) in Table 1] and its derivatives, in solution (Scheffer, Jennings & Louwerens, 1976) and the solid state (Dzakpasu, Phillips, Scheffer & Trotter, 1976), has revealed unusual reaction pathways. Photolysis of (I) in solution gives products resulting from intramolecular /3-H abstraction.…”

Section: Introductionmentioning

confidence: 99%

The crystal and molecular structure of cis-4a,5,8,8a-tetrahydro-1,4-naphthoquinone and comparison with some of its derivatives

Phillips¹,

Trotter²

1977

Acta Crystallogr Sect B

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Organic photochemistry. 16. Photochemical hydrogen abstraction reactions proceeding through five-membered transition states. Product control through restriction of rotation in diradical intermediates

Cited by 19 publications

References 13 publications

The crystal and molecular structures of solid-state photodimers of two cis-4a,5,8,8a-tetrahydro-1,4-naphthoquinone derivatives

The crystal and molecular structures of solid-state photodimers of two cis-4a,5,8,8a-tetrahydro-1,4-naphthoquinone derivatives

Trapping of o-quinodimethane with p-quinones: synthesis of tetrahydro-1,4-anthracenediones

The crystal and molecular structure of cis-4a,5,8,8a-tetrahydro-1,4-naphthoquinone and comparison with some of its derivatives

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