Preparation of phenanthrenes by photocyclization of stilbenes containing a tosyl group on the central double bond. A versatile approach to the synthesis of phenanthrenes and phenanthrenoids

Journal of Organic Chemistry

Volumn 75, Issue 20, 2010, Pages 6764-6770

  Neo, Ana G ^a,b   López, Carmen ^a   Romero, Victor ^a   Antelo, Berta ^a   Delamano, José ^a   Pérez, Antonio ^a   Fernández, Dolores ^a   Almeida, Jesús F ^a   Castedo, Luis ^a   Tojo, Gabriel ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

IRRADIATION;

DOUBLE BONDS; PHOTOCYCLIZATION; PROTOCOL CANS; SULFONYL GROUPS; UV IRRADIATION;

ANTHRACENE;

HETEROCYCLIC COMPOUND; PHENANTHRENE DERIVATIVE; PHENANTHRENOID DERIVATIVE; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLIZATION; SYNTHESIS; ULTRAVIOLET IRRADIATION;

EID: 77957889288     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100742e     Document Type: Article

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66. The mechanism does not seem to involve a carbon-sulfur bond breakage, resulting in a carbon radical that would abstract a proton from the solvent, as irradiation of p -tolyl p -tolylmethyl sulfone and allyl p -tolyl sulfone in the presense of DBU leads to recovery of the starting compounds. In both compounds a carbon-sulfur bond breakage would be particularly easy as it would produce very stabilized p -methylbenzyl or allyl radicals.