30796-92-0Relevant articles and documents
Selective Functionalization in the Bay Region of Polycyclic Aromatic Hydrocarbons via Dilithiation
Ashe, Arther J.,Kampf, Jeff W.,Salva, Paresh M.
, p. 5558 - 5559 (1990)
Sequential reaction of policyclic aromatic hydrocarbons with butyllithium/TMEDA hexane and electrophiles allows preparation of derivatives functionalized in the bay region.
Photodeoxygenation of phenanthro[4,5-bcd]thiophene S-oxide, triphenyleno[1,12-bcd]thiophene S-oxide and perylo[1,12-bcd]thiophene S-oxide
Chintala, Satyanarayana M.,Petroff II, John T.,Barnes, Andrew,McCulla, Ryan D.
, p. 503 - 515 (2019/05/29)
Sulfoxides, upon irradiation with ultraviolet (UV) light undergo α-cleavage, hydrogen abstraction, photodeoxygenation, bimolecular photoreduction, and stereo-mutation. The UV irradiation of dibenzothiophene S-oxide (DBTO) yields dibenzothiophene (DBT) as a major product along with ground-state atomic oxygen [O(3P)]. This is a common method for generating O(3P) in solution. The low quantum yield of photodeoxygenation and the requirement of UVA light are drawbacks of using this method. The sulfoxides benzo[b]naphtho-[1,2,d]thiophene S-oxide, benzo[b]naphtho [2,1,d]thiophene S-oxide, benzo[b] phenanthro[9,10-d]thiophene S-oxide, dinaphtho- [2,1-b:1’,2’-d]thiophene S-oxide, and dinaphtho[1,2-b:2’,1’-d]thiophene S-oxide have shown to deoxygenate up to three times faster than DBTO upon UVA irradiation; however, the photodeoxygenation of these sulfoxides does not appear to be limited to the production of O(3P). In this work, phenanthro[4,5-bcd]thiophene S-oxide, triphenyleno[1,12-bcd]thiophene-S-oxide, and perylo[1,12-bcd]thiophene-S-oxide were synthesized and their photodeoxygenation was studied. Phenanthro[4,5-bcd]thiophene-S-oxide, triphenyleno[1,12-bcd]thiophene-S-oxide, and perylo[1,12-bcd]thiophene-S-oxide deoxygenated upon UVA irradiation. However, the common intermediate experiments did not conclusively identify the photodeoxygenation mechanism of these sulfoxides.
The Insertion and Extrusion of Heterosulfur Bridges. XV. S-Bridging of 2,2'-Binaphthyl and 1-(2-Naphthyl)cyclohexene. Studies on Hydrodehalogenation During the Reaction
Klemm, L. H.,Stevens, Michael P.,Tran, Long K.,Sheley, John
, p. 1111 - 1116 (2007/10/02)
Regioselectivity occurs in the sulfur-bridging reactions of 2,2'-binaphthyl (1) and 1-(2-naphthyl)cyclohexene (7) by means of hydrogen sulfide and a chromia-alumina-magnesia catalyst (designated I) in a flow apparatus at 550 deg C.Thus, 1 gives a higher yield (6.1percent of dinaphthothiophene from 1,1'-bridging than of dinaphthothiophene (3.4percent) from 1,3'-bridging.No product expected from 3,3'-bridging was identified.Substrate 7 undergoes both dehydrogenation and bridging to yield 2-phenylnaphthalene (8percent), benzonaphthothiophene (9percent) from alpha briding, and benzonaphthothiophene (3percent) from beta bridging into the naphthalene ring.Exploratory studies showed that either sulfided catalyst I or a sulfided molybdenum(VI) oxide-alumina-cobalt(II) oxide catalyst (II) effects hydrodehalogenation of various monohalo- and polyhaloarenes (where halo, X, is chloro or bromo) at 450-550 deg C.In the biphenyl, phenanthrene, naphthalene, and pyrene systems, halogen was lost either under sulfur-bridging conditions or under hydrogenolysis conditions, i.e. with methanol as a reactant.For every substrate the parent arene was isolated or identified as a reaction product.In selected experiments, acid HX was also identified in the effluent.Use of hydrogen sulfide as a reactant led to formation of dibenzothiophene and phenanthrothiophene as main products in the biphenyl and phenanthrene systems, respectively; while use of methanol as a reactant gave small amounts of methyl bromide (for X = Br) and methylarenes.
