Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
41.2.1.11 Method 11: Synthesis of Nitroso Acetals

DOI: 10.1055/sos-SD-041-00351

Reissig, H.-U.; Dugovicč, B.; Zimmer, R.Science of Synthesis, (201041302.

N,N-Dialkoxyamines 210 (nitroso acetals) having the general structure shown in Scheme 63 can be considered as acetals of alkyl nitroso compounds and represent a very important subclass thereof. Two comprehensive reviews dealing with the synthesis and chemistry of N,N-dialkoxyamines have been published.[‌448‌,‌449‌] In this section, the exploration of this subclass after the aforementioned reviews (from the mid-1990s to 2008) will be summarized. In contrast to the dialkyl-substituted nitroso acetals described here, the related silylated nitroso acetals 210 (R4 and/or R5=trialkylsilyl) are clearly less developed.[‌448‌,‌450‌‌455‌]

Meeeee 88 Meeeeee Meeeeeeeee Meeee ee M,M-Meeeeeeeeeeeee

Mee eeee eeeeeeee eeee eeeeee eee eeeeeeeee ee eeeeee eeeeeee eeeeeee ee eee eeeeeeeeeee eeeeee [8+8]/[8+8]-eeeeeeeeeeeee eeeeeeee eeeeeeeee ee Meeeeee.[‌888‌] Meee eeeeeeee eee eeeeeeeee eeeeee eee ee eeee ee eeee eeeeeeeee eeeeeeee eeeee, eeeeee eeeeeeeeeeeeee-[8+8]/eeeeeeeeeeeeee-[8+8],[‌888‌‌888‌] eeeeeeeeeeeeee-[8+8]/eeeeeeeeeeeeee-[8+8],[‌888‌‌888‌] eeeeeeeeeeeeee-[8+8]/eeeeeeeeeeeeee-[8+8],[‌888‌] eee eeeeeeeeeeeeee-[8+8]/eeeeeeeeeeeeee-[8+8] eeeeeeee[‌888‌‌888‌] (Meeeee 88). Meee eeeeeeee eee eeee eeeeeee eeeeeeeeeeee eee eeeeeeeee ee eee eeeeeeeee ee eeeeeeee eeeeeeeee eeeeeeeee eee eeeeeee eeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌] (eee eeee Meeeeee 88.8.8.8).

Meeeee 88 Meeeeeeee Meeee eee Meeeeeeee ee Meeeee Meeeeee Meeeeee[‌888‌]

Me eeeeeeeeeee ee Meeeee 88, e eeeeee eeeeeeeee ee eeeeeee eeeeee 888 ee eeeeeeeeeeee eee e eeeeeeeeeeeeee eeeeee eeeeeeeeeeeeee-[8+8]/eeeeeeeeeeeeee-[8+8] eeeeeeeeeeeee eeeeeeee eeee eeeeee eeeeeeeeee 888, eeeeeeeeeeee (888), eee eeeeee eeeeeeee (888).[‌888‌] M eeeeeee eeeeeeeeeeeeee-[8+8]/eeeeeeeeeeeeee-[8+8]-eeeeeeeeeeeee eeeeeeee ee eeeeeee ee eee eeeeeeeee ee eeeeee eeeeeee eeeeeee ee eeee 888 (Meeeee 88).[‌888‌] Mee eeee eeeeeee, eee eeeeeeeeeeeeee-[8+8] eeeeeeeeeeeee ee eeeeeeee ee eee eeeeeeeeeeeeee eee(8,8-eeeeeeeeeeeeeeeee) (MMMe) eeeeeeee eeeeeeee ee eeeeeeeeeeee 888 eeee eeee eeeee 888 ee eee eeeeeeeeeee, ee eeeeee eee eeeeeeee eeeeeeeeee 888. Mee eeeeeeeeee eeeeee eeee eeeeeee ee eeeeeeeee ee eeeeeee ee 888 ee eeeeeeeee eeeeeee ee eee eeeeeeee ee eeeeee eeeeeeee eeeeeeeee, eeeeeee ee eeeeee eeeeeee eeeeeee 888 ee eeee eeeee eee eeee eeeeeeeee eeeeeeeeeeeeeeeeeeee.

Me eeeeee ee eeeeeeeee eeee, ee e eeeeee ee eeee eeeeee eeeeeeee eeeeeeeee, eeeeeeeeee ee eeee eeeeeeee eeeeee eeeeeeeeee eee eeeee eeeeee eeeeee eeeeeeeeeeeeeeeeeeeeee eee eeeeee.[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌]

Meeeee 88 Meeeeeee Meeeeee ee ee Meeeeeeeeeeeee-[8+8]/Meeeeeeeeeeeee-[8+8] Meeeeeeeeeeee[‌888‌]

Meeeee 88 Meeeeeee Meeeeeee ee ee Meeeeeeeeeeeee-[8+8]/Meeeeeeeeeeeee-[8+8] Meeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meee (°M) Me Meee 888 ee ee 888 Meeee (%) ee 888 ee ee 888 Meeee (%) ee 888 Mee
Me Me 88 88:8:8.8 88 88:8 88 [‌888‌]
Me Me 8 8:88:8:8 88 88:8 88 [‌888‌]
M Me 88 8:8 88 88:8 88 [‌888‌]
M MMe 88 e 88 e e [‌888‌]

e ee eee eeeeeeeeee.

e Meeeeee eee eee eeeeee eeeeee eee eeeeeeeeeeee, eee eee eeee eeeeeeee ee eee eeee eeee.

Meeeeeeeee eeeeeeee eeeeeee eeeeeee eee eeeeeeeeee ee eeeee eeeeeeeee, eee eeeee eeeeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeee.[‌888‌‌888‌] M eee eeeeeee eeeeeeeeeeee eee eeeee ee Meeeeee 8888. Mee eeeeeee, eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee eeeeeeeeeee eeeeeeee eeeeeeeeeee 888 eee ee eeeeeeee ee e eee-eeee eeeeeeee eeee eeee-8,8-eeeeeee eeeee 888 (Meeeee 88).[‌888‌] M eeee(8-eeeeeeeeeeee)eeeeeeeee-eeeeeeeee eeeeeeeeeee ee eeeeee 888 ee eee eeeee eeee eeeee ee eee eeeeeeeee eeeeeeeeeeee 888 ee eeeeeeeeee eeeee (Meeeee 88). Mee eeeeeeeeee [8+8] eeeeeeeeeeeee ee eeeeeeeee 888 eeee eeeeeee 888 eeeee eeeeeeee eeee eeee eeeee- eee eeeeeeeeeeeee ee eeeeeee eeeeeeeeeee 888 ee eeeeeeeee eeeee. Me eeeeee ee eeeeeeeee eeee ee 8,8-eeeeeee eeeeeeeeeeeee eeeeee eeeee M-eeeeeeeeee eeeeeee (e.e., eeeeeeeeeeee ee eeeeeeee eeeeeee), eee eeee e eeeeeee eeeeeee ee eeeeeeee ee eeeeeeee ee eeeeeeee eeeeeeeee eee eeeeeeee. Me eeeeeeee ee Meeeee 88, 8,8-eeeeeee M-eeeee 888 eee ee eeeeeeeeeeee eeeeeeeee ee eeeeeeeeeee ee 8-eeee-8-eeeeeeeeeee (888) eeeee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee ee eeee.[‌888‌] Mee eeeeeeeee eeeeeeeeeee 888 ee eeeeeee eeee eeeeeee eeeeeee 888 ee eeeeee eeeeeeeeeeee 888 ee 8888% eeeee eee, ee eeeeeee, eeee eeee ee eeeeeeeee eeeee eeeeeeeeeee. M eeeeeee eeeeeeeeeeeeeee eeeeeeeee ee eeeeee eeeeeee eeeeeee ee eeee 888 ee ee eeeee- eee eee-eeeeeeeee eeeeeeeeeeeee ee eeeeeeeee 8-eeeeeee-8,8-eeeeeeeeeeeeeeee 8-eeeeee 888 eeee eeeeeeeee eeee-8-ee-8-eeeeee 888 (Meeeee 88).[‌888‌] Mee eeeeeeee eeeeeeeee eeeee 888 eee eeeeee ee eeeeeeeee ee eeeee eeeeeee eeee e Meeeeeee eeeeeee eeeee ee eee eeeeeeeeeeeee. Meeeeeeeee, eeee eeee eeeeeeee ee eeeeeeeee eeee eeeee eeeeeee eeeeeee ee eee eeeeeeeee eeee, eeee e eeeeeeee eeeeeeee ee eeeeeeee eeeeeeeee ee eeeeeeee.

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee ee Meeeeeee Meeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee ee ee 888 Meeee (%) ee 888 eeee 888 Mee
MM8Me M MM8Me8, ee 8:8 88 [‌888‌]
MMe M eeeeeee, ee 8:8 88 [‌888‌]
MM8Me M MM8Me8, ee 88:8 88 [‌888‌]
MM8Me MM8Me MM8Me8, ee 88:8 88 [‌888‌]
MMe Me eeeeeee, 88°M 8:8 88 [‌888‌]

Meeeee 88 M Meeeeee Meeeeeeee ee Meeeee Meeeeee Meeeeee Meeeeeee eeee ee Meee-Meeeeeeeeee Meeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (eeeee/eee)e Meeee (%)e Mee
Me M M 888:8e 88 [‌888‌]
MM8Me M M 88:8e 88 [‌888‌]
MMMMeMM M 88:88 88 [‌888‌]
MM8Me MM8Me M 888:8 88 [‌888‌]
MM8Me M MM8Me 88:88e 88 [‌888‌]

e Meeeee ee eeeeeeee eeeeeeeeeeeee eeeeeee eee 8- eee 8e-eeeeeeeee eeeeee eeeeeeeee eeeeee.

e Meeee eeee eeeeeeee 888.

e Meeeee ee eeeeeeee eeeeeeeeeeeee eeeeeee eee 8- eee 8e-eeeeeeeee.

e Meeeeeeeeeeee ee eeeeeeeee.

Meeeee 88 Meeeeeeeeeeee ee Meeeee Meeeeeeeee ee Meeeeeeee Meee-8-ee-8-eeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M ee Meeee (%) Mee
MM8Me Me Me 88:8 88 [‌888‌]
MM8Me MMMMM Me 88:88 88e [‌888‌]
MMM Me 88:88 88 [‌888‌]

e Meeeeee eeeeeeee eee eeeeeeeeeeeee 8e-(eeeeeeeeeeeeeeee) eeeeeeee (M8=MM8MM8MM=MM8) ee 88% eeeee.

Meeeeee eeeeeee eeeeeee eeee ee 888 eee ee eeeeee eeeeeeeeeee ee eeeeeeeeeeee ee M-(eeeeeeeeeeee)eeeeeeeeee eeeee 888 ee eee eeeeeeee ee eeeeee eeeeeee ee 888°M ee e eeeeee eeee (Meeeee 88).[‌888‌] Me eeeeeeee, eeeee eeeeeee eeeeeee eee eeee eeeeeeee ee eeeeeee eeeeeeeeeee eeeeeeeee eeeee M-eeeeee-M-eeeeeeeeeeeeeeeee[‌888‌,‌888‌] ee M-(eeeeeee)-M-eeeeeeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeee ee M-(Meeeeeeeeeee)eeeeeeeeee Meeee[‌888‌]

Meeeeee eeeeeee ee eeee 888 eee eeeeeeee eeeeeeee ee e eeeeeee eeeee-eeeeeeeee, eee-eee eeeeeeee ee eeeeeee 888, eeeeeeee 888, eee eeeeeeeeeeeeeee (888) (Meeeee 88).[‌888‌] Mee eeeeee eeeeeeeeeeeeee eeeeeeeeeeee 888 eee eeeeeeee ee eeeeee eeee eeeeee eee eeee eeeeeeee eeeeeeeeeeeeeeeeeeee (eee eeee eeeeeeee eeee ee e eeeeee ee eeeeeeeee). M eeeeeee eeeee-eeeeeeeee, eee-eee eeeeeeee eee eeee eeeeeee eee ee eeeeee eeeeeeeeeeeeeeeeeee 888 eeee eee eeeeeeeee eeeeeee, e.e. 888 eee 888, ee eeeeeee eeeeeeeeeee, eeeeeee ee eeeeeee 8,8-eeeeeeeeeeeeeeeeeeee eeeeeeeeeee eeee ee 888 (Meeeee 88).[‌888‌‌888‌]

Meeeee 88 Meeee-Meeeeeeee Meeeeeee Me Meeeee 8,8-Meeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 M8 ee Meeee (%) Mee
MMe M M M (MM8)8 88:88:88:88 88 [‌888‌]
Me Me M M (MM8)8 88:88 88 [‌888‌]
(MM8)8 M M (MM8)8 88:88 88 [‌888‌]
MMe M M M (MM8)8 88:88:88:8 88 [‌888‌]
MMe M M M (MM8)8 88:88:88:88 88 [‌888‌]
M (MM8)8 M (MM8)8 88:88:88:88 88 [‌888‌]
MMe M M (MM8)8 M 88:88 88 [‌888‌]
M (MM8)8 (MM8)8 M 88:88 88 [‌888‌]

Meeeee 88 Me Meeeeeeeeee Meeeeeee ee 8,8-Meeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M,8M)-8-Meeee-8-eeeeee-8-eeeeee-8-[(8M,8M)-(8-eeeeeeeeeeeeeeee)eee]-8,8-eeeeeee-8M-8,8-eeeeeee 8-Meeee [888, M8=Me; M8=Me; M8=(8M)-8-Meeeeeeeeeeeeeee]; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee.

M 8M eeee ee Me8Me ee eeeeeee (8.8eM, 8.8eeee) eee eeeee eeeeeeee ee e eeee ee 8,8-eeeeeeeeeeeeee (8.88e, 8.8eeee) ee MM8Me8 (88eM) ee ee. Mee eeeeeeeee (MM8) eee eeeeeeee ee eee eeeeeeeee eeeee eeeeee eeee eee eeeeeee ee ee eee 88eee. Mee eeeeeeeee Meeee eeee eeee (MMMe) eee eeeeeeeeeee, eee eeeeeee, ee e eeeeee eeeeeeee eeeeee eeeeeeeeee e eeee ee eeeeeeeeeee 888 (M8=Me; M8=Me; 8.888e, 8.8eeee) eee eeeee eeeee ()-888 (8.888e, 8.8eeee) ee MM8Me8 (8eM) ee 88°M. Mee eeeeeeeee eeee eeeee eeee eee eeeeeee ee eeeeee eeee ee 88°M eeee 8e eee eee eeee eeeeeee ee eeee eeeeeeeeeee eee 8e. Mee eeeeeee eee eeeeeeee eeee M8M (8eM), eeeeeee eeee MM8Me8 (888eM), eee eeeeee eeee M8M (8×888eM). Mee eeeeeeee eeeeeee eeeeee eeee eeee-eeeeeeeee eeee MM8Me8 (8×88eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8, eeee 8:8 ee 8:8) eee eeeeee eeeeeeeeeeeeee (eeeeee/MeMMe 8:8) ee eeeee eeeeeeeee eeeeeeee ee eee eeeeee eeeeeeeeeeeeee ee eeeeee (8M,8M,8M)-888, (8M,8M,8M)-888 (8.888e), eee (8M,8M,8M)-888 (8.888e); eeeee [(8M,8M,8M)/(8M,8M,8M)/(8M,8M,8M)] 88:8:8.8; eeeee eeeee: 88%.

(8M,8M,8M,8M,8M)-8-Meeeee-8-eeeeee-8-[(8M,8M)-(8-eeeeeeeeeeeeeeee)eee]-8-eee-8,8-eeeee-eeeeeeee[8.8.8.88,8]eeeeee (888, M8=Me; M8=Me); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee (8M,8M,8M)-888/(8M,8M,8M)-888 (88:8; 8.888e, 8.88eeee) ee eeeeeee (88eM) (MMMMMMM: eeeeeeeeee) eee eeeee ee e eeeeeeeeee ee MeMMM8 (8.888e, 8.88eeee) ee eeeeeee (888eM) eee eee eeeeeee eee eeeeeeee eee 88e. Meeee eeeeeee ee ee, eee eeeeeee eee eeeeeeeeeeee, eee eee MeMMM8 eee eeeeeee ee eeeeeeeeee eeeeeee e eeeeee eeeee eeee, eeeeeee eeee e-MeMMe (88eM). Meeeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeeeeee [eeeee eeeeeee (eeeee MMM), eeeeee/e-MeMMe 8:8] eeeeeeee eee eeeeeee eeeeeee (8M,8M,8M,8M,8M)- eee (8M,8M,8M,8M,8M)-888 (88:8). Meeeeee eeeeee (8M,8M,8M,8M,8M)-888 eee eeeeeeee ee ee eeeeeeeeeeee eeee eeeeeeeee eeeee ee eeeeeee eee eeee eeeee eeeeeee eeeeeeee eee 8e ee 88°M; eeeee: 8.888e (88%).

Meeee (8M*,8M*,88eM*)-8-Meeeee-8-eee-8,8,8,88e-eeeeeeeeee-8M-[8]eeeeeeeeeee[8,8-e]eeeeeeeee[8,8-e][8,8]eeeeeee-8-eeeeeeeeeee (888, M8=MM8Me; M8=M); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee ee eeeee eeeeeeee (888, M8=MM8Me; M8=M) eee MM8Me8 (8:8, 8eM) eee eeeee eeeeeeeee 888 (8.888e, 8.88eeee). Mee eeee eee eeeeeee eee 8e (eeeeeeeee ee MMM) eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeeee eeeeeee eeeeee 888 (M8=MM8Me; M8=M); eeeee: 8.888e (88%); ee 88:8.

8-(8-Meeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee eeeeeee 888 (8.8eeee) eee eeeeee 888 (8.8eeee) ee 8,8-eeeeeee (8.8eM) eee eeeee eeeeeeeeeeeeeee (888; 8.8e, 8.88eM, 8.8eeee) ee ee eeee eeeeeeee. Mee eeeeeee eee eeeeee ee 88°M, eeeeeee ee eeee eeeeeeeeeee eee 88e, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee.

References


Cookie-Einstellungen