Dihydropyrane Addition Products

Woods, G. Forrest; Kramer, David N.

doi:10.1021/ja01201a520

Cited by 113 publications

(33 citation statements)

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“…The chemical shifts for several bicyclic 1,3-dioxans have been reported (10). For compound 26 the predicted shifts for C-5, C-7, and C-11 are 42, 33, and 42 ppm, respectively.…”

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confidence: 99%

¹³C chemical shift data for 1,7-dioxaspiro[5.5]undecanes and related compounds

Pothier¹,

Rowan²,

Deslongchamps³

et al. 1981

Can. J. Chem.

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. Can J. Chem. 59, 1132 (1981). The carbon-13 chemical shift data for a series of 1,7-dioxa-, 1-oxa-7-thia-, and 1,7-dithiaspiro[5,5]undecanes and related compounds are presented. Analysis of this data led to structural and stereochemical assignments. The results show that the unsubstituted spiro bicyclic compounds exist in the conformation shown as conformation a . It is shown that the 13C chemical sbift parameters developed for cyclohexane derivatives can be applied to the sulfur but not to the oxygen heterocycles.NORMAND POTHIER, DARYL D. ROWAN, PIERRE DESLONGCHAMPS et JOHN K. SAUNDERS. Can. J. Chem. 59, 1132 (1981). Les deplacements chimiques en rmn de 13C de plusieurs derives de dioxa-1,7, oxa-1-thia-7 et dithia-1,7 spiro [5,5]undecanes sont presentes ainsi que ceux de quelques composes modkles. Les structures et la stereochimie des composes ont tte attribuees a partir de I'analyse de ces donnees. L'analyse conformationnelle demontre que les composes spiro-bicyclique non substitues existent dans la conformation a . On demontre que les parametres de deplacement chimique de 13C developpes pour les derives du cyclohexane peuvent &tre appliques aux heterocycles sulfures mais ils ne peuvent pas &tre utilises pour les composes oxygenes.

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“…The chemical shifts for several bicyclic 1,3-dioxans have been reported (10). For compound 26 the predicted shifts for C-5, C-7, and C-11 are 42, 33, and 42 ppm, respectively.…”

mentioning

confidence: 99%

¹³C chemical shift data for 1,7-dioxaspiro[5.5]undecanes and related compounds

Pothier¹,

Rowan²,

Deslongchamps³

et al. 1981

Can. J. Chem.

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“…The reaction of 16 with NH,OAc in a mixture of toluene/MeCN 1 : 1 at 70" afforded compound 17 which was the starting material for the synthesis of macrobicycle 3-5. Treatment of 'monochloro-diethyleneglycol' with dihydropyran [30] gave the protected alcohol 18 which was condensed with the tris(sodium salt) of 17 leading to 19. Removal of the tetrahydropyranyl group was achieved in the presence of TsOH in EtOH/H,O 95:5 under reflux [31].…”

Section: L] [2])mentioning

confidence: 99%

“…layer washed 3x with H20, dried (Na2S04), and evaporated affording pure 16 (110 g, 99%) as a solid. This compound was used directly for the following step, m. 1-Chloro-5-(tetrahydro-2H-pyran-Z-yloxyJ-3-oxopentane (18) was synthesized according to the procedure given in [30]. To monochlorodiethyleneglycol (56 g, 0.45 mol) and CH2C1, (150 ml), a soln.…”

Section: 4'4"-tritosyi-777-nitrilo/ri(4-uzuheptunenirrile) (12)mentioning

confidence: 99%

Synthesis of Macrobicyclic Polyamines by Direct Macrobicyclisation via Tripode‐Tripode Coupling

Dietrich¹,

Hosseini²,

Lehn³

et al. 1985

Helvetica Chimica Acta

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“…According to the literature it is a classical acid catalysed reaction [1]. Numerous catalysts have been used for the tetrahydropyranylation of hydroxyl groups such as conventional mineral or organic acids like concentrated hydrochloric acid [2], p-toluenesulphonic acid [3] and Lewis acids (e.g. boron trifluoride etherate [4] or zirconium tetrachloride [5]).…”

Section: Introductionmentioning

confidence: 99%