Allenes-41: The addition of thiols to allenyl-and phenylpropynyl-nitrile and the formation of thiazolines and benzothiazoles
SR Landor, PD Landor, ZT Fomum, JT Mbafor
Index: Landor, Stephen R.; Landor, Phyllis D.; Fomum, Z. Tanee; Mbafor, J. Tanyi; Mpango, George W. B. Tetrahedron, 1984 , vol. 40, # 11 p. 2141 - 2149
Full Text: HTML
Citation Number: 2
Abstract
Thiols add to allenylnitriles to give unconjugated nitriles which may be isomerised to conjugated enesulphide nitriles either at high temperature (200°) or with base. Phenylpropynenitrile gives conjugated adducts directly. Heating the conjugated adducts from aminoethanethiols at> 200° results in 5-exotrig ring closure and elimination of acetonitrile to give thiazolines and benzothiazoles.
Related Articles:
Reactions of alkylmercurials with heteroatom-centered acceptor radicals
[Russell, Glen A.; Ngoviwatchai, Preecha; Tashtoush, Hasan I.; Pla-Dalmau, Anna; Khanna, Rajive K. Journal of the American Chemical Society, 1988 , vol. 110, # 11 p. 3530 - 3538]
Alkylation of. beta.-substituted styrenes by a free radical addition-elimination sequence
[Russell, Glen A.; Tashtoush, Hasan; Ngoviwatchai, Preecha Journal of the American Chemical Society, 1984 , vol. 106, # 16 p. 4622 - 4623]
Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids
[Zhao, Wei-Ming; Chen, Xiao-Lan; Yuan, Jin-Wei; Qu, Ling-Bo; Duan, Li-Kun; Zhao, Yu-Fen Chemical Communications, 2014 , vol. 50, # 16 p. 2018 - 2020]
Nickel-complex-catalyzed cross-coupling of grignard reagents with 2-halogenobenzothiazoles
[Babudri, F.; Florio, S.; Ronzini, L.; Aresta, M. Tetrahedron, 1983 , vol. 39, # 9 p. 1515 - 1521]
[Wang, Zhanglin; Tang, Riyuan; Xiao, Qin Chinese Journal of Chemistry, 2011 , vol. 29, # 2 p. 314 - 320]