{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T10:32:14Z","timestamp":1782901934757,"version":"3.54.5"},"reference-count":14,"publisher":"American Chemical Society (ACS)","issue":"9","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2001,5,1]]},"DOI":"10.1021\/ol015711w","type":"journal-article","created":{"date-parts":[[2002,7,26]],"date-time":"2002-07-26T04:56:38Z","timestamp":1027659398000},"page":"1327-1330","source":"Crossref","is-referenced-by-count":21,"title":["Double Allylation Reactions of (2-Azaallyl)stannanes:\u2009 Synthesis of <i>N,N<\/i>-Bis(3-butenyl)amines and Their Conversion to 2,3,6,7-Tetrahydroazepines via Ring-Closing Metathesis"],"prefix":"10.1021","volume":"3","author":[{"given":"William H.","family":"Pearson","sequence":"first","affiliation":[{"name":"Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109-1055"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aaron","family":"Aponick","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109-1055"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2001,4,3]]},"reference":[{"key":"ol015711wb00001\/ol015711wb00001_1","first-page":"3617","volume":"63","author":"Pearson W. H.","year":"1998","journal-title":"J. Org. Chem."},{"key":"ol015711wb00002\/ol015711wb00002_1","doi-asserted-by":"crossref","first-page":"1345","DOI":"10.1021\/ja00030a031","volume":"114","author":"Pearson W. H.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ol015711wb00003\/ol015711wb00003_1","doi-asserted-by":"crossref","first-page":"853","DOI":"10.1021\/ja00211a024","volume":"110","author":"Sawyer J. S.","year":"1988","journal-title":"J. Am. Chem. Soc."},{"key":"ol015711wb00004\/ol015711wb00004_1","first-page":"396","volume-title":"Comprehensive Organic Synthesis","volume":"1","author":"Selected","year":"1991"},{"key":"ol015711wb00005\/ol015711wb00005_1","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1021\/jo00201a037","volume":"50","author":"Keck G. E.","year":"1985","journal-title":"J. Org. 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Chem."},{"key":"ol015711wb00012\/ol015711wb00012_1","unstructured":"Representative Procedure:\u2009 Preparation of Diene 17b.Allylmagnesium bromide (2.2 mL of a 1.0 M solution in ether, 2.2 mmol) was added in a dropwise fashion to a solution of the imine16a(0.374 g, 1.00 mmol) in THF (5 mL) at \u221278 \u00b0C. After 30 min, phenyl chloroformate (0.344 g, 2.20 mmol) was added and the mixture was allowed to warm slowly to room temperature, then diluted with water and ether. The organic layer was separated, and the aqueous layer was extracted 3\u00d7 with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (0\u22123% ethyl acetate\/hexanes gradient) gave 0.230 g (80%) of diene17bas a clear colorless oil.1H NMR (CDCl3, 400 MHz, room temperature, rotomers present)\u03b47.44-7.07 [m, 5 H containing 7.36 (app t,J= 6.6 Hz), 7.18 (app t,J= 7.2 Hz), 7.09 (app t,J= 7.2 Hz)], 5.89\u22125.73 (m, 2 H), 5.16\u22125.01 (m, 4 H), 3.69 (app br s, 1 H), 3.27\u22123.17 (m, 2 H), 2.53\u22122.33 (m, 4 H), 1.90 (app br s, 1 H), 1.02 (app t,J= 6.4 Hz), 1.00 (app d,J= 3.2 Hz), 0.98 (app d,J= 3.2 Hz), 1.04\u22120.98 (total 6 H).13C NMR (CDCl3, 100 MHz)\u03b4155.22, 151.59, 151.47, 135.94, 135.57, 135.41, 129.56, 129.20, 125.11, 125.02, 121.75, 121.70, 117.15, 116.78, 116.55, 116.41, 64.48 (br), 45.02 (br), 35.31, 34.95, 34.34, 32.98, 31.49, 31.00, 20.49, 20.41, 20.34."},{"key":"ol015711wb00013\/ol015711wb00013_1","first-page":"2056","volume":"36","author":"Recent","year":"1997","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ol015711wb00014\/ol015711wb00014_1","first-page":"89","volume":"32","author":"For","year":"1999","journal-title":"Aldrichimica Acta"},{"key":"ol015711wb00015\/ol015711wb00015_1","first-page":"1033","volume":"1031","author":"Osipov","year":"2000","journal-title":"Synlett"}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol015711w","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,13]],"date-time":"2023-03-13T21:55:16Z","timestamp":1678744516000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol015711w"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2001,4,3]]},"references-count":14,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2001,5,1]]}},"alternative-id":["10.1021\/ol015711w"],"URL":"https:\/\/doi.org\/10.1021\/ol015711w","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2001,4,3]]}}}