5-Aza-2,8,10-trithiaadamantan or Trithiotrimorpholine

Craig, D. P.; Shipman, J. J.; Hawthorne, and M. Frederick; Fowler, Ray B.

doi:10.1021/ja01610a057

Cited by 14 publications

(2 citation statements)

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“…The combined benzene extracts were dried with MgS04 and evaporated. The solid residue was recrystallized from 30 ml of ethanol; yield, 1.2 g (60%); mp 124-126°; infrared spectrum (KBr) showed peaks at 6.03, 6.13, 6.89, 8.64, 13.44, and 14.28 µ) nmr (CS2), r singlet 2.85 (10), multiplet 3.08 (1), singlet 4.38 (1), doublet 7.80 and 8.45 (8).…”

Section: XI Experimental Sectionmentioning

confidence: 99%

Reactions of phenylmagnesium bromide with sterically hindered cyclobutanones. III. Mechanism of Grignard addition to these carbonyl groups

Kimbrough¹,

Askins²

1967

J. Org. Chem.

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Section: XI Experimental Sectionmentioning

confidence: 99%

Reactions of phenylmagnesium bromide with sterically hindered cyclobutanones. III. Mechanism of Grignard addition to these carbonyl groups

Kimbrough¹,

Askins²

1967

J. Org. Chem.

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“…with MgS04 and evaporated. The solid residue was recrystallized from 30 ml of ethanol; yield, 1.2 g (60%); mp 124-126°; infrared spectrum (KBr) showed peaks at 6.03, 6.13, 6.89, 8.64, 13.44, and 14.28 µ) nmr (CS2), r singlet 2.85 (10), multiplet 3.08 (1), singlet 4.38 (1), doublet 7.80 and 8.45 (8).…”

mentioning

confidence: 99%

Hexahydro-1,3,5-trithia-6-azacyclopenta[cd]pentalene

Fort¹,

Semon²

1967

J. Org. Chem.

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NOVENBER 1967 gave starting material in 90% recovery: mp 125-128' (lit.* mp 132-133"); mmp 129-131".Reaction of V with Phenylmagnesium Bromide in Tetrahydrofuran at 65". Synthesis of I-Cyclohexenyl Benzhydryl Ketone (VI).-The phenylmagnesium bromide from 10 g of bromobenzene and 5 g of magnesium in 50 ml of ether was decanted from excess magnesium. About half the ether was distilled off, 50 nil of dry tetrahydrofuran was added, and the solvent was distilled off until the boiling point reached 65".A solution of 2.0 g of V in 15 ml of tetrahydrofuran was added. The mixture was refluxed for 20 hr. The brown reaction mixture was cooled in ice and 50 ml of water was added dropwise wit,h swirling followed by 15 ml of concentrated hydrochloric acid. The resulting mixture was extracted three times with 20 ml of benzene. The combined benzene extracts were dried with MgS04 and evaporated. The solid residue was recrystallized from 30 ml of ethanol; yield, 1.2 g (60%); mp 124-126'; infrared spectrum (KBr) showed peaks at 6.03, 6.13, 6.89, 8.64, 13.44, and 14.28 p ; nmr (CS,), T singlet 2.85 (lo), multiplet 3.08 singlet 4.38 ( l ) , doublet 7.80 and 8.45 ( 8 ) . ilnal. Calcd for C2~H?00: C, 86.8; H, 7.3. Found: C, 86.9; H, 7.4. Reaction of VI1 with Phenylmagnesium Bromide. Synthesis Registry No.-VI, 4173-56-2; VII, 14002-01-8 ; VIII, 13958-56-0; X, 14002-02-9; XI, 13958-57-1 ; phenylmagnesium bromide, 100-55-3. (17) L. I. Smitil and H. H. Hoelin, 0.y. Sun., 20, 47 (1940). (18) Thic melting point of a mixture of VI1 and X mas 98-113'.

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Bridged 6/6 Ring Systems

1961

Chemistry of Heterocyclic Compounds: A Series of Monographs

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5-Aza-2,8,10-trithiaadamantan or Trithiotrimorpholine

Cited by 14 publications

References 0 publications

Reactions of phenylmagnesium bromide with sterically hindered cyclobutanones. III. Mechanism of Grignard addition to these carbonyl groups

Reactions of phenylmagnesium bromide with sterically hindered cyclobutanones. III. Mechanism of Grignard addition to these carbonyl groups

Hexahydro-1,3,5-trithia-6-azacyclopenta[cd]pentalene

Bridged 6/6 Ring Systems

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