Photochemistry of cyclic, saturated β-keto-sulphides

Maheshwari, Karuna; Berchtold, Glenn A.

doi:10.1039/c2969000013a

Cited by 13 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Spirocyclic compounds 16 − 19 were synthesized from the corresponding α,β-unsaturated esters 7 − 10 . Compounds 7 and 8 were readily obtained from N -tosylazetidin-3-one ( 5 ) and thietan-3-one ( 6 ), respectively. Previous syntheses of ketone 6 were rather low yielding and difficult to reproduce with larger amounts of material; therefore, we developed a new synthesis from commercially available dibromide 21 (Scheme ).…”

mentioning

confidence: 99%

Synthesis and Structural Analysis of a New Class of Azaspiro[3.3]heptanes as Building Blocks for Medicinal Chemistry

et al. 2010

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Synthesis and Structural Analysis of a New Class of Azaspiro[3.3]heptanes as Building Blocks for Medicinal Chemistry

et al. 2010

View full text Add to dashboard Cite

show abstract

“…The products formed by photolysis with 2537-A light are consistent with homolytic cleavage of the C-S bond followed by diradical addition to the adjacent double bond to form product 13 which on further irradiation produces 14. The formation of 14 from 13 is analogous to the photochemical behavior of other substituted episulfides.…”

Section: Light-inducedmentioning

confidence: 61%

“…-7( 13) 42 (24) C-4 1527 (7) 409 (13) 5575 ( 8) 85 ( 6) 417 ( 26) 86 (7) -102 (21) -29 (12) 50 (25) C-5 880 ( 7) 2100( 11) 5575 ( 8) 100 ( 6) 269 ( 21) 116…”

Section: Experimental Section40unclassified

Photochemical transformations of small-ring heterocyclic compounds. XXXII. Photochemical transformations in the 9-heterobicyclo[3.3.1]nonenone system

Padwa¹,

Battisti²

1972

J. Am. Chem. Soc.

View full text Add to dashboard Cite

non-6-en-2-one (1) and its 9-oxa analog have been found to rearrange principally to methyl 5,6-dihydro-2//-pyran-2-propionate derivatives upon irradiation in methanol. When the irradiation of the thia system was carried out in deuteriomethanol, the product formed was found to have incorporated the deuterium atom in the thiapyran portion of the molecule. Irradiation of the oxa analog in deuteriomethanol, however, gave ester which had the deuterium atom located adjacent to the carbonyl group. This result indicates that the thia system is significantly different from its oxa analog in its photobehavior and that carbonyl-sulfur interactions in the excited state play an important role in the photochemistry of cyclic ß-keto sulfides. Wavelength and solvent effects were also observed in the photochemistry of 1. Possible mechanistic pathways to the observed photoproducts are discussed. 8 H) in the nmr.The mass spectrum of 3a shows the Mechanism A

show abstract

Four‐Membered Sulfur Heterocycles

Dittmer

Sedergran

1985

Chemistry of Heterocyclic Compounds: A Series of Monographs

View full text Add to dashboard Cite

Photochemistry of cyclic, saturated β-keto-sulphides

Cited by 13 publications

References 0 publications

Synthesis and Structural Analysis of a New Class of Azaspiro[3.3]heptanes as Building Blocks for Medicinal Chemistry

Synthesis and Structural Analysis of a New Class of Azaspiro[3.3]heptanes as Building Blocks for Medicinal Chemistry

Photochemical transformations of small-ring heterocyclic compounds. XXXII. Photochemical transformations in the 9-heterobicyclo[3.3.1]nonenone system

Four‐Membered Sulfur Heterocycles

Contact Info

Product

Resources

About