TY - JOUR
T1 - Sequential intermediates in the base-catalyzed conversion of bis(π-conjugated propargyl) sulfones to 1,3-dihydrobenzo- and naphtho[c]thiophene-2,2-dioxides
AU - Zafrani, Yossi
AU - Gottlieb, Hugo E.
AU - Sprecher, Milon
AU - Braverman, Samuel
PY - 2005/11/25
Y1 - 2005/11/25
N2 - In a recent article, we reported on the base-catalyzed rearrangements of dipropargyl selenides, -Sulfides, -sulfoxides, and -sulfones that eventually lead to polycyclic aromatic products. In the present work, we report on the first isolation and characterization of the thiophene dioxide intermediates 5b,c from a mild tandem isomerization/cyclization/aromatization of bis(π-conjugated propargyl) sulfones. Monoallene 2b,c and diallene 3b intermediates were also identified by NMR. A kinetic study of the rearrangement of 1a-c revealed that the unusual facile tandem process is highly dependent on the nature of γ-substitution.
AB - In a recent article, we reported on the base-catalyzed rearrangements of dipropargyl selenides, -Sulfides, -sulfoxides, and -sulfones that eventually lead to polycyclic aromatic products. In the present work, we report on the first isolation and characterization of the thiophene dioxide intermediates 5b,c from a mild tandem isomerization/cyclization/aromatization of bis(π-conjugated propargyl) sulfones. Monoallene 2b,c and diallene 3b intermediates were also identified by NMR. A kinetic study of the rearrangement of 1a-c revealed that the unusual facile tandem process is highly dependent on the nature of γ-substitution.
UR - http://www.scopus.com/inward/record.url?scp=28044443152&partnerID=8YFLogxK
U2 - 10.1021/jo051692i
DO - 10.1021/jo051692i
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AN - SCOPUS:28044443152
SN - 0022-3263
VL - 70
SP - 10166
EP - 10168
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -