Allylic Rearrangements. XV. The Carbonation of Butenylmagnesium Bromide

Lane, John F.; Roberts, John D.; Young, William G.

doi:10.1021/ja01232a013

Cited by 23 publications

(22 citation statements)

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“…( = 7, 6 H); 1.38 (d, J = 7, 2 H); 1.87 (m, 1 H); 2.24 (d, J = 7, 4 H); 4.85-5.25 (4 H); 5.87 (m, 2 H). MS M " ) , 141 (7), 85 (56), 57 (loo), 55 (25), 41 (17). /yl-l.(i-/iepludien-4-ol(7) (76% yield from methyl cyclopentariecarboxylate).…”

Section: Experimental Partmentioning

confidence: 99%

“…(dd,.l=7,2,3H); 2.65(tq,J=7,7,1H); 6.20(br.d,J= 15,lH); 6.89(dq,J= 15,7,1H).MS:126(0,M+'),lll (6), 98 (9), 69 (loo), 41 (22). (25) (28),83(100).69 (15),55(80),41(23). 6.88 (m, 1 H).…”

Section: -Merhli-l-hepten-4-onementioning

confidence: 99%

“…I H); 5.94 (m, I H). MS: 126 ( I , M+'), 85 (25), 69 (7), 57 (IOO), 55 (6), 41 (41). : 126 (4, M +).…”

Section: 5-~imrthyl-i-hepten-l-onementioning

confidence: 99%

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β‐Cleavage of Bis(homoallylic) Potassium Alkoxides. Two‐Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar‐Turmerone, α‐Damascone, β‐Damascone, and β‐Damascenone

Snowden

Linder

Müller

et al. 1987

Helvetica Chimica Acta

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~ ~~The transformation of 36 bis(homoallylic) alcohols VIl to alkenones IX and X via /I-cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf. Scheme 2). These studies have established an order of /]-cleavage for 2-propenyl, l-methyl-2-propeny1, 2-methyl-2-propeny1, 1, I-dimethyl-2-propeny1, and benzyl groups in alkoxides 49a-56a and have allowed a comparison between the /I-cleavage reaction and the oxy-Cope rearrangement in alkoxides 74a 83a. As illustrative synthetic applications, a two-step preparation of propenyl ketoncs 1 5 4 2 from carboxylic esters is dcscribcd, together with syntheses of' or-turmerone (48), cc-damascone ((E)-71), a-damascone ((E)-109) and /I-damasccnone ((I?)-1 11).

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Section: Experimental Partmentioning

confidence: 99%

“…(dd,.l=7,2,3H); 2.65(tq,J=7,7,1H); 6.20(br.d,J= 15,lH); 6.89(dq,J= 15,7,1H).MS:126(0,M+'),lll (6), 98 (9), 69 (loo), 41 (22). (25) (28),83(100).69 (15),55(80),41(23). 6.88 (m, 1 H).…”

Section: -Merhli-l-hepten-4-onementioning

confidence: 99%

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β‐Cleavage of Bis(homoallylic) Potassium Alkoxides. Two‐Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar‐Turmerone, α‐Damascone, β‐Damascone, and β‐Damascenone

Snowden

Linder

Müller

et al. 1987

Helvetica Chimica Acta

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“…1. A Grignard reagent prepared from 2-methyl-3-butenyl bromide 2 4 ) was reacted with an alt Pheromone Synthesis. Part XL VII.…”

mentioning

confidence: 99%

“…The residue was distilled to give 4.3 g (73.7%) of lla, bp 98 ~ 104°C (2 mmHg (Z ) ) and p-toluenesulfonic acid (50 mg) were added to a solution of lIa (3 g) in ether (17 ml). After stirring for 3 hr at room temperature, the mixture was washed with potassium carbonate solution, dried over potassium carbonate and concentrated in vacuo to give 4.3g (quantitative) 4,) was added to a stirred and ice-cooled solution of lIb (4.3 g) in methylene chloride (30 ml). The stirring was continued for 2 hr at 0 ~ 5°C.…”

mentioning

confidence: 99%