NOVEL CHEMICAL BEHAVIOR OF A [2,3]SIGMATROPIC REARRANGEMENT PRODUCT OF 2-PHENYLTETRAHYDROTHIOPYRANIUM 1-METHYLIDE

Authors
DOI S SHIRAI N SATO Y
Citation
S. Doi et al., NOVEL CHEMICAL BEHAVIOR OF A [2,3]SIGMATROPIC REARRANGEMENT PRODUCT OF 2-PHENYLTETRAHYDROTHIOPYRANIUM 1-METHYLIDE, Journal of the Chemical Society. Perkin transactions. I (Print), (14), 1998, pp. 2181-2184
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I (Print) → ACNP
ISSN journal
0300922X
Issue
14
Year of publication
1998
Pages
2181 - 2184
Database
ISI
SICI code
0300-922X(1998):14<2181:NCBOA[>2.0.ZU;2-O
Abstract
1,3,4,5,6,11a-Hexahydro-7E-2-benzothionine 5, which is a [2,3] sigmatr opic rearrangement product of 2-phenyltetrahydrothiopyranium 1-methyli de 8,has been synthesized by reaction of 1-methyl-2-phenyltetrahydroth iopyranium triflate 3 with sodium amide in liquid ammonia or by the fl uoride ion-induced desilylation of trans-2-phenyl-1-[(trimethylsilyl)m ethyl] tetrahydrothiopyranium perchlorate trans-7. Compound 5 is stabl e at room temperature and reverts to ylide 8 by ring-opening.