Flash Pyrolysis of Selenides. Syntheses of Bibenzyls, Olefins, and Related Compounds

Abstract

Pyrolyses of a series of selenides and diselenides were studied. Selenides and diselenides bound with an active methylene group like benzyl gave a variety of substituted bibenzyls and related ethane derivatives in high yields. Other diselenides were easily caused to cleave to give various aromatic and aliphatic olefins in good yields together with elemental selenium. Lepidopterene, [2.2]paracyclophane, and benzocyclobutene were prepared by thermal cleavage of their corresponding phenylselenomethyl-substituted compounds as an application of the pyrolysis concerned.

Dramatic solvent and concentration dependence in the reaction of (anthracen-9-yl)methanamines with suitable electron-deficient acetylenes

“…As expected, product distribution changed under different conditions. However, a few products arising through either single electron transfer mediated transformations such as 9‐methylanthracene ( 7 ), 9‐anthraldehyde ( 6 ), 1,2‐bis(9‐anthracenyl)ethane ( 8 ) and lepidopterene ( 9 ) or through reaction with adventitious oxygen such as 9,10‐anthraquinone ( 5 ) were common in all reactions (Chart ). In most cases, acetylenes underwent oligomerization to intractable residues.…”

Self-Assembled Monolayers of Organoselenium Compounds on Gold: Surface-Enhanced Raman Scattering Study

“…Gold foil (0.05 mm thick), BSe, DPDSe, and DBDSe were purchased from Aldrich. DODSe (8) and BPSe (9) were prepared according to the previously published methods.…”

(Anthracen-9-yl)methyl sulfides as a mechanistic probe for chemical as well as photochemical electron-transfer reactions

“…Various fractions were collected and analyzed using spectroscopic measurements. The products formed were identified as 9-anthraldehyde (3), 63 9,10-anthraquinone (6), 64 9-methylanthracene (12), 65 1,2-bis(9-anthracenyl)ethane (13), [66][67][68][69] lepidopterene (14), 66,[70][71][72][73][74] biplanene (15), [75][76][77] anthrone (16) 78 along with products arising through the S-alkyl residues present in parent anthracenemethyl sulfides. Common products formed in the photoirradiation of (anthracen-9-yl)methyl sulfides 1a-f are shown in Chart 2 and details of all the products isolated are presented in Scheme 3.…”