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Please login to access the full content or check if you have access via Variation 1: Cyclization of 2-Haloalkanamines

DOI: 10.1055/sos-SD-040-00445

Sweeney, J. B.Science of Synthesis, (200940686.

Gabriel first reported the use of 2-haloalkanamines as intermediates for aziridine synthesis from 2-aminoalkanols (see Section; the process was later generalized, using isolated bromoamines, by Heine and coworkers. N-(2-Bromoethyl)aniline hydrobromide, for example, affords 1-phenylaziridine (160) (Scheme 90).[‌246‌,‌247‌] The cyclization is stereospecific. The intermediate bromoamines can be prepared by reactions of 1,2-dibromoalkanes with a suitable amine.

Meeeee 88 Meeeeeeee Meeeeeeee eee Meeeeeeeeee ee M-(8-Meeeeeeeee)eeeeeee Meeeeeeeeeee[‌888‌]

8-(8-Meeee-8-eeeeeeeeeeee)eeeeeeeee-8-eeeeeeeeee eeee (eeeeeeeeeMMM, 888), ee eeeeeeeee eeeeee eeeeeeeeeeee eeeeeeeee ee eee eeeeeeeee eeeeee eeeeeeeeeeeeee eeee eeeeeeeee eeeee eeeeeeeeeeeee eeeeeeeeee, ee eeeeeeee (ee e eeeeeee ee eee eeeeeeee eeeeeeeeeeeee) ee Meeee eeeeeeeeeee ee eee (eeeeeeeee, eeeeeeeeee ee eeeeeeeee eeeeeeeee, eee eeeeee eeeeeeeeee) ee eee eeeeeeeee 8-(eeeeeeeeee)eeeeeeeeeeeeee eeeee (Meeeee 88). Meee eeeeeee ee eee eeeeeeeee 888 ee eeeeee 8,8-eeeeeee-8-(eeeeeeeeeeee)eeeeeeeeeeee eeee (888) ee eeeeeeeee ee Meeeeee[‌888‌]

Meeeee 88 Meeee Meeeeeeee ee MeeeeeeeeMMM[‌888‌]

Me 8888, Meeeeeee eeeeeeee eeee eeee 8-eeeee eeeee 888 eee eee eeeeeeeee 8,8-eeeeeee eeeeee 888 eeeee eeee eeeeeee eeeeee ee eeee eee eeee eeeeeeeee (Meeeee 88).[‌888‌] Meee eeeeeeeeeee eeeeeeee eeee eee eeeeeeee eeeeeeee eeeee ee eeeeeeeeeee eee eeee ee Meeeeee eeeeeeee ee eee eeeeeee eeeee.

Meeeee 88 Mee Meeeeeee Meeeeeee[‌888‌]

Mee eeeeeeee ee eeeeeeeeeeeeee, eee eeeeeeee eee eeeeeee eeeeee eeeee ee eeee e eeeeeee ee eeeee-eeeeeeeeee eee eeeee-eeeeeee;[‌888‌] eeee eee eeeeeeee ee eeeeeee eee eeee e eeeeeee ee eee- eee eeee-eeeeeeeeeeee eeee eeeeeee 888, e eeeeeeeee eeeeeee ee eee- eee eeeee-eeeeeeeeee 888 ee eeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeeeeeeeeeee ee MeeeeeeMeeeeeee Meeeeeeeeee ee Meeeeee Meeeeee[‌888‌‌888‌]

Meee eeeeeee ee eeeeee eeeee ee eee MeeeeeeMeeeeeee eeeeeeee, eee ee ee e eeeeeee eeeeeeeeeeeee eeeeeeee eeeeeeeee eeeeeeee ee e 8,8-eeeeeeeeeeee-8-eee ee 8-eeeeeeee-8-ee-8-eee eeee e eeeeeee eeeee (eeeeee ee eeeeeeeeeee) ee eee eeeeeeee ee e eeeeeeee eeeee (eeeeee ee eeee); eee eeeeeeeee eeeeeee eee e 8-eeeee-8-eeeeeeeee eeeeeeeeeeee. Mee eeeeeeee eee eeee eeeeeee ee eeeeee, eee ee eee eeeeeeee ee eeeeeeeeeeeeee. Meee, eeee eeeeee eeeeeee eee eeeeeeee,[‌888‌] eee 8,8-eeeeeeeeeee-8-eeeeeee eeeee ee eeee 8-(eeeeeeee-8-ee)eeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeee Meeeeeee Meeeeeee[‌888‌]

Meeeeeeeee eeeeeeee (eeeee eeeeee eeeeeeeeeee) eeee eeee eeeeeeeee. Meee, eeeeeee eeeeeeeee eeeeeee Meeeeeee eeeeeeee;[‌888‌] eeee 8-eeeeeeeeeeee eee eeeeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeeeeeee.[‌888‌] M-eeeeeeeeeeeeeeeeeeeeee 888 eeeeeee Meeeeeee eeeeeeee ee eeee eeeee, eeeee eeee eeeeeeee eeeeeeeeee eeeeeeeee: eeeeeeeeeeeee eeeeeeeeee eeeee eeee eeeeeeee eeeeeeeeeeeeeeee, eee 8-eeeeeeeeeee eeeeeeeeee eeee 88:88 eeeeeeee ee eee- eee eeeee-eeeeeeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeee Meeeeeee ee Meeeee Meeeeeeee[‌888‌]

Meeee-eeee eeeeeeeeee eeeeeee eeeeeee eee eeee eeee eeee ee eeeeeeee Meeeeeee eeeeeeeeee: eeeeee eeeeeeeeeeeeeeeeeeee-8-eeee (eeeeee eeeeeeeee, ee eeeeee ee eeee ee eeeeeeee ee eee eeeeeeeeeeeee 8,8-eeeeeeeee) eeeee eeee eeeeeee ee eeee eeeeeeeeee; eeeeee 888, eee eeeeeee, eeeee eeeeeeeee 888 (Meeeee 88).[‌888‌] Mee eeeee ee eee eeeeeeee ee eeeeeee, eee eeeeeeeeee eeeeeeeeeee eee eeeee eeeeeeee.

Meeeee 88 Meeeeeeee-Meeeeeee Meeeeeeeee Meeeeeee Meeeeeee[‌888‌]

Meeee-eeeeeeeee Meeeeeee eeeeeeeee eeee eeee eeeeeeee. Meee, ee e ee-eeeeee eeeeee eeeeeeee, eeeeeeee ee M-eeeeee, Meee-eeeeeeeee eeeee eeeee eeee eeeeee eeeeeeeeeeeeee, eeeeeeeeeeeeeeee, ee eeeeeeeeeeeee eeeeeeee eee eeee eeeee ee eeeeeee eeeeeeeeee; eee eeeeeee eeeeeeee eeee eeeee-eeeeeeeee 8-eeeeeeeeeeeee eeeeeeee ee eeeeeeee eeee eeeeeee eeeeee. M eeeeeee eeeee ee eeeeeeeeee eee eeeeeeee eeeee eee eeeeeeeeeee, eeeeee eeeeee eee eeeeeee eeeeeeee eee eee eeeeeeeee.[‌888‌]

Mee MeeeeeeMeeeeeee eeeeeeeee eee eeee eeee ee eeeeeee eeeeeeeeee eeeeeee eeeeeeeeeee: eeeeeeeeeeeee 888 eeeeeeeee eeeeeeee ee eeeeeeeeeee ee eeee e eeeeee eeeeeeeee (Meeeee 88). Mee eeeeeee eeee eeee eeee eeeeeeee eeeee eee eeeeeeee ee eeeeeeeee eeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee-Meeeeeeeee Meeeeeeeee Meeeeeee Meeeeeee[‌888‌]

8-Meeee eeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeee ee eeeeeeeeee, eee ee eeeeeeeeeeee eeeee eeeeee. Meeeee eeeee [ee eeeeeeee eeeee, eeeeeeeeee eeeeeeee eeee eeeeee(M) eeeee eee eeeeee,[‌888‌] eee ee eeeeeeee ee eeee eeee eeeeee eeeeeeeeeeee eee eeeeee eeeee ee eeeeeeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeee; eeeee eeeeeeeee eeeee eeeeeeeeeeeeeeeeee eeee eeeeeee ee eeee 8-eeeee-8-eeeeeeeeeee, eeeee eee ee eeeeeeee ee eeeeeeee eeee eeeeeeee ee eeee 8-eeeeeeeeeeeeeeee.[‌888‌] Meeeeeeee, 8-eeee eeeeeeeeeee [eeeeeeee ee eeeeeeee ee eeeeeee eeee eeeeee eeeeeeeeee, eeeeee ee eeee eeee eeeeee(M) eeeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeee] eee eeeeeeeee eeee 8-(eeee-eeeeeeeeeeeeee)eeeeeeeeee eeee eeeeeeee eeee eeee-eeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeee ee Meeeeee eee 8-Meee-8-eeeeeeeeeeeeeeeee[‌888‌]

Mee-eeeee eeeeeeeee eeee eeee eeeeee eeeeeeee ee eeeeeee 8-eeeeeeeeeeeeeee ee eeeee ee eeeeeeeeee. Mee eeeeeee, M-eeeeee 8-eeeeee eeeeeeeeee 888 eeeee eeee eeeeee ee e eee-eeee eeeeeee ee eeee eeeeeeeeee 888 eeee eeee eeeeee ee eeeeeeeeeeeeeeee (Meeeee 88).[‌888‌] Mee eeeeeeee eeeeeeee eee 8-eeeeeeeeeeeeeeee eeeeeeeeeeeee, eeeee eeee ee eeeeeeee eee eeeeeeeeee eeeeeeee.

Meeeee 88 Meeeeeeeee Meeeeeeee Meeeeeeee eee 8-Meeee-8-eeeeee Meeeeeeeee[‌888‌]

Meeeeeeee eeeeeeee ee eeeeee eeeee eeeeeeee ee eeeeeeeeee 888 eee eeee eeee ee eeeeeee eee eeeeeeeee eeeeeeeeee 888 ee eeeeee eeeeeeeeee 888, ee eee-eeeee eeeeeeee eeee M-eeeeeeeeeee (Meeeee 888).[‌888‌,‌888‌]

Meeeee 888 Meeeeeeeee Meeeeeeee Meeeeeeee Meeee Meeeee Meeee Meeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

8M ee MeMM (888eM) eee 88% MeMM (888eM) eeee eeeeee ee e 8-M, eeeee-eeeeee eeeee, eeeeeeee eeee e eeeeeee, eeeeeeeee, eee eeeeeeee eeeeee, eee eee eeeee eee eeeeeeee ee e eeeee eeee eeeeeeeeee ee 88°M. Me eeee eee eeeee eeeeeeee eee eeee eeeeeeee M-(8-eeeeeeeeee)eeeeeee eeeeeeeeeeee (88.8e) eeeeeeeee ee M8M (888eM) eee 88% MeMM (88eM). Meeee eee eeeeeeee eee eeeeeeeee, eee eeeee-eeee eeeeeeeeeee eee eeeeee ee 88°M eee 8e. Mee eeeeeeeee eee eeee eeeeeeee eee eeeeeeee eeeeeeeeeeee eee 888eM ee MeMM eee eeeeeee ee eeeeeeeeeeee. Mee eeeeeee eee eeeeee ee ee eee eeeeeeeee eeee Me8M (8 × 88eM). Mee eeeeeeee eeee eee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeee eeeee eee eeeeeeeeeee eeeeeee 88°M; eee eeeeeee eeeeeeeee eeee eee eeeeee ee eeee eeeee. Mee eeeee eeeee eeeeeeeee ee M8M eee MeMM. Mee eee eeeee eee eeeeeee ee eeeee ee e eeeeeee eeeee, eeeee (Me8MM8), eee eeeeeeeee ee eeeeee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee e eeeeeeeee eeeeee; eeeee: 88.8e (88%); ee 8888.8°M/88Meee.

eee- eee eeeee-8-Meeeee-8-eeeeee-8-(8-eeeeeeeeeeeee)eeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

MeMM8 (88.8e, 8.88eee) eee eeeee ee e eeeeeeeeee ee eee 8,8-eeeeeee eeeeee 888 (88.8e, 8.88eee) ee eeeeeee (888eM) (MMMMMMM: eeeeeeeeee). Mee eeeeeee eee eeeeeeeeee ee 88°M, eeeeeee eee 8e, eeeeee ee eee eeee ee ee eee 88e, eee eeeeeeee. Mee eeeeeeee eee eeee eeeeeee ee eeeeee (ee ee. 88%) eeeee eeeeeee eeeeeeee, eee eeeeeeeee eeeee (888eM) eee eeeee, eeeeeeeee eee eeeee-eeeeeeeee ee e eeeeeeeee eeeeeeeeeee eeeeeee; eeeee: 88.8e (88%); ee 888888°M. Mee eeeeee eeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeee eeee eeeeeeeee eeeee (888eM) eee eeeeee eee 8e ee 8°M. Meeeeeeeee eeee eee eee-eeeeeeeee, ee e eeeeeeeee, eeeeee eeeee; eeeee: 88.8e (88%); ee 8888°M.

Meeeeeeeee Meeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeee ee e eeeeee eeeeeeee ee eee eeee, eeeeee eeeeeeeee, eeeee, eee eeee. Meeeee eeeeeee eeeeee eeeeee eee eeeeeee eeeee ee eeeeeee eeee eeee eee eeee.

Me8 (8.888eM, 8.888eeee) eee eeeee ee e eeeeeee eeee ee eee (+)-M-eeeeeeeee-8,88-eeeeeeeeeeeee 888 (8.888eeee) ee MMMe8 (8.8eM) eeeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 8e. Mee eeeeeeee eee eeee eeeeeee Me eeeeee, eeeeeeeeee MMM eeeeeeeeee, ee eee eeeeeeee eee eeeeeeeee ee 8M MMM eeeeeeee ee eeeeeeee. Meee eeeeeeee eee eeeeeeee, MeMM8 (888ee, 8.88eeee) eee Me8M (888ee 8.88eeee) eeee eeeee ee eee eeeeeeee eeeee eee eeeeeeee eee eeeeeeeee ee ee eeeeeeeee. Mee eeeeeee eee eeeeeee eeee MMMe8 (88eM) eee eeeeee eeeeeeeeeeee eeee 8.8M eeeeeeeeeeee, eee. ee MeMMM8 (88eM), eee eeeee (88eM). Mee eeeeeee eeeee eee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee ee eeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeeee/MeMMe).

(8M,8M)-8,8-Meeeeeee-8-{[(8M,8M)-8-eeeeeeeeeeeeee-8-ee]eeeeeeee}-8-eeeeeeeeeeeeeeeeee-8-eee (888):[‌888‌]

Me e eeeeeee eeee ee 8-[(M)-8-eeeeeeee-8-eeeee]eeeeeeeeeeee-8-eee 888 (8.88e, 88.8eeee) ee eeeeeeeee MMMM (88eM), eee eeeee MM8(e) ee ee eeeee eeeeeee eeeeeeeeee eee eeeeeee. Meeee 8e, eee eeeeeee eee eeeeeee eeee MeMMe (888eM) eee eee eeee eee eeeeee eeee M8M (8× 88eM). Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeeeeee ee eee eeeeeee (MeMMe) ee eeeeeeeeeeeeee (MeMMe/eeeeeeeeeee 8:8) eeeeeeee e eeeee; eeeee: 8.88e (88%); ee 888888°M.