TY - JOUR
T1 - Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane
AU - Li, Yuan Qiang
AU - Thiemann, Thies
AU - Mimura, Keisuke
AU - Sawada, Tsuyoshi
AU - Mataka, Shuntaro
AU - Tashiro, Masashi
PY - 1998/9
Y1 - 1998/9
N2 - The oxidative cycloaddition of 3,4-dibromo-[n](2,5)thiophenophanes 12b-e and (2,4)[8]thiophenophane 16 with dienophiles gave stereoselectively O=S-bridged cycloadducts 18, 19 and 24. The X-ray analysis of cycloadduct 18a shows it to have a rigid conformation. The molecules can be regarded as a new series of paddlanes. Under the same oxidative conditions, 3,4-dibromo-[8](2,5)thiophenophane (12a) gave the two dimers 29 and 30. The results of the X-ray analysis of 29 are discussed.
AB - The oxidative cycloaddition of 3,4-dibromo-[n](2,5)thiophenophanes 12b-e and (2,4)[8]thiophenophane 16 with dienophiles gave stereoselectively O=S-bridged cycloadducts 18, 19 and 24. The X-ray analysis of cycloadduct 18a shows it to have a rigid conformation. The molecules can be regarded as a new series of paddlanes. Under the same oxidative conditions, 3,4-dibromo-[8](2,5)thiophenophane (12a) gave the two dimers 29 and 30. The results of the X-ray analysis of 29 are discussed.
KW - Oxidative Diels-Alder reaction
KW - Thiophenophane S-monoxide
KW - Thiophenophanes
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U2 - 10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p
DO - 10.1002/(sici)1099-0690(199809)1998:9<1841::aid-ejoc1841>3.0.co;2-p
M3 - Article
AN - SCOPUS:0002167428
SN - 1434-193X
SP - 1841
EP - 1850
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 9
ER -