Stereospecific synthesis and absolute configuration of optically active diaryl(acyloxy)(alkoxy)spiro-λ4-sulfanes
作者： Dénes Szabó , Szilárd Szendeffy , István Kapovits , Árpád Kucsman , Mátyás Czugler
DOI: 10.1016/S0957-4166(97)00245-0
关键词:
摘要: Abstract Optically active (R)-(+)-1,1′-spirobi[3H-2,1-benzoxathiol]-3-one (R)-(+)- 5 , the (R)-(+) and (S)-(−) enantiomers of spiro[3H-2,1-benzoxathiol-1,1′-naphtho[1,8-d,e]-3H-2,1-oxathiin-3-one] 8 (S)-(−)- (S)-(+)-spiro[3H-2,1-benzoxathiol-3-one-1,1′-naphtho[1,8-d,e]-3H-2,1-oxathiine] (S)-(+)- 10 all belonging to class diaryl(acyloxy)-(alkoxy)spiro-λ4-sulfanes (spirosulfuranes) were prepared by dehydration optically diaryl sulfoxides 4 7 9 respectively, them carrying reactive CH2OH COOH substituents. (R)-(+)-5H,7H-dibenzo[c,f]-1,5-oxathiocin-5-one 12-oxide 6 a sulfoxide-lactone isomer spiro-λ4-sulfane was also obtained from dehydration. The molecular structures including absolute configurations determined for X-ray diffraction method. Relevant bond length angle data are listed. Sulfur configurations, solid-state conformations stereospecific pathway discussed in detail.
elsevier.com
sci-hub.se 参考文章(21)
A. Kucsman, I. Kapovits, Nonbonded sulfur-oxygen interaction in organic sulfur compounds Studies in organic chemistry. ,vol. 19, pp. 191- 245 ,(1985)
I. G. Csizmadia, A. Mangini, F. Bernardi, Organic sulfur chemistry : theoretical and experimental advances Elsevier Science Publishers , Distributors for the U.S. and Canada, Elsevier Science Pub. Co.. ,(1985)
I. Kapovits, J. Rábai, F. Ruff, Á. Kucsman, B. Tanács, Diaryldiacyloxyspirosulfuranes—II Tetrahedron. ,vol. 35, pp. 1875- 1881 ,(1979) , 10.1016/0040-4020(79)80013-7
I. Kapovits, J. Rábai, F. Ruff, Á. Kucsman, Diaryldiacyloxyspirosulfuranes—I Tetrahedron. ,vol. 35, pp. 1869- 1874 ,(1979) , 10.1016/0040-4020(79)80012-5
Linus Pauling, The Nature of the Chemical Bond ,(1939)
Stig Allenmark, Sofia Claeson, Chromatographic resolution of a C2-symmetric spirosulfurane : 1,1'spirobi[3H-2,1-benzoxathiol]-3,3'-dione Tetrahedron-asymmetry. ,vol. 4, pp. 2329- 2332 ,(1993) , 10.1016/S0957-4166(00)80095-6
L. J. Adzima, Chian C. Chiang, Iain C. Paul, J. C. Martin, Sulfuranes. 35. Synthesis, reactions, and crystal and molecular structure of a sulfurane with two apical nitrogen-centered ligands: a spirodiazasulfurane Journal of the American Chemical Society. ,vol. 100, pp. 953- 962 ,(1978) , 10.1021/JA00471A050
J. Drabowicz, J.C. Martin, Optically active spirosulfuranes via nonclassical resolution with 2,2′-dihydroxy 1,1′-binaphthol Tetrahedron: Asymmetry. ,vol. 4, pp. 297- 300 ,(1993) , 10.1016/S0957-4166(00)86072-3
D. Szabó, I. Kapovits, Á. Kucsman, P. Huszthy, Gy. Argay, M. Czugler, V. Fülöp, A. Kálmán, T. Koritsánsky, L. Párkányi, Spirosulfuranes with different heteroatoms in axial positions A comparison of NS(IV)O and NS+(IV)⋰O systems Journal of Molecular Structure. ,vol. 300, pp. 23- 46 ,(1993) , 10.1016/0022-2860(93)87004-S
William Y. Lam, Eileen N. Duesler, J. C. Martin, A comparison of hypervalent bond polarizabilities in sulfuranes (10-S-4 species) and persulfuranes (12-S-6 species) Journal of the American Chemical Society. ,vol. 103, pp. 127- 135 ,(1981) , 10.1021/JA00391A024